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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
2-chloro-4-(tert-butoxy)-6-cyclopropylpyrimidine 2-chloro-4-(tert-butoxy)-6-cyclopropylpyrimidine 1412959-25-1 C11H15ClN2O
2-Chloro-4-(thiazol-4-yl)-1,3,5-triazine 2-Chloro-4-(thiazol-4-yl)-1,3,5-triazine 1417519-63-1 C6H3ClN4S
2-Chloro-4-cyclopentyl-6-(iso-propyl)pyrimidine 2-Chloro-4-cyclopentyl-6-(iso-propyl)pyrimidine 1412953-28-6 C12H17ClN2
2-chloro-4-ethyl-6-(iso-propyl)pyrimidine 2-chloro-4-ethyl-6-(iso-propyl)pyrimidine 1412953-12-8 C9H13ClN2
2-Chloro-4-phenyl-6-(iso-propyl)pyrimidine 2-Chloro-4-phenyl-6-(iso-propyl)pyrimidine 1412961-58-0 C13H13ClN2
2-Chloro-5-Acetoxypyrimidine 2-Chloro-5-Acetoxypyrimidine 1303967-57-8 C6H5ClN2O2
2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,5-d3 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,5-d3 2241869-93-0 C11H15BClNO2
2-Cyano-6-(oxan-4-yl)pyridine-4-boronic acid pinacol ester 2-Cyano-6-(oxan-4-yl)pyridine-4-boronic acid pinacol ester 2223048-34-6 C17H23BN2O3
2-cyclobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-cyclobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 1795453-09-6 C14H21BN2O2
2-cyclopentyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2-cyclopentyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2223028-94-0 C17H23BF3NO2
2-cyclopropyl-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclopropyl-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223012-12-0 C14H19BFNO2
2-Cyclopropyl-5-cyanopyridine-3-boronic acid pinacol ester 2-Cyclopropyl-5-cyanopyridine-3-boronic acid pinacol ester 2223052-02-4 C15H19BN2O2
2-Ethyl-6-(N-Boc-piperidin-3-yl)pyridine-4-boronic acid pinacol ester 2-Ethyl-6-(N-Boc-piperidin-3-yl)pyridine-4-boronic acid pinacol ester 2223003-85-6 C23H37BN2O4
2-Fluoro-6-(2-trifluoromethylphenyl)pyridine 2-Fluoro-6-(2-trifluoromethylphenyl)pyridine 1261754-91-9 C12H7F4N
2-Fluoro-6-(cyclohexyl)pyridine 2-Fluoro-6-(cyclohexyl)pyridine 1563529-03-2 C11H14FN
2-Fluoro-6-(n-propyl)pyridine 2-Fluoro-6-(n-propyl)pyridine 1563529-55-4 C8H10FN
2-Fluoro-6-(oxan-3-yl)pyridine 2-Fluoro-6-(oxan-3-yl)pyridine 1563531-06-5 C10H12FNO
2-fluoro-6-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-fluoro-6-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223045-48-3 C16H23BFNO3
2-Fluoro-6-ethylpyridine 2-Fluoro-6-ethylpyridine 1309113-04-9 C7H8FN
2-HYDROXY-3-(2-FLUOROPHENYL)PYRIDINE 2-HYDROXY-3-(2-FLUOROPHENYL)PYRIDINE 1214330-31-0 C11H8FNO
2-Hydroxy-3-(2-tolyl)pyridine 2-Hydroxy-3-(2-tolyl)pyridine 1261993-59-2 C12H11NO
2-Hydroxy-3-(iso-butyl)pyridine 2-Hydroxy-3-(iso-butyl)pyridine 1417518-46-7 C9H13NO
2-Hydroxy-3-(pyrimidin-5-yl)pyridine 2-Hydroxy-3-(pyrimidin-5-yl)pyridine 1417518-04-7 C9H7N3O
2-Hydroxy-4-(1H-imidazol-1-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(1H-imidazol-1-yl)-6-(iso-propyl)pyrimidine 1412953-97-9 C10H12N4O
2-Hydroxy-4-(1H-pyridin-2-one)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(1H-pyridin-2-one)-6-(iso-propyl)pyrimidine 1412955-32-8 C12H13N3O2
2-Hydroxy-4-(2-fluorophenyl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(2-fluorophenyl)-6-(iso-propyl)pyrimidine 1412957-43-7 C13H13FN2O
2-Hydroxy-4-(2-furyl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(2-furyl)-6-(iso-propyl)pyrimidine 1412959-67-1 C11H12N2O2
2-Hydroxy-4-(2-tolyl)-6-(tert-butyl)pyrimidine 2-Hydroxy-4-(2-tolyl)-6-(tert-butyl)pyrimidine 1412953-13-9 C15H18N2O
2-Hydroxy-4-(2-trifluoromethylphenyl)-6-cyclopropylpyrimidine 2-Hydroxy-4-(2-trifluoromethylphenyl)-6-cyclopropylpyrimidine 1412956-04-7 C14H11F3N2O
2-Hydroxy-4-(3-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(3-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 1412959-35-3 C13H21N3O
2-hydroxy-4-(3-thienyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(3-thienyl)-6-(tert-butyl)pyrimidine 1412961-02-4 C12H14N2OS
2-Hydroxy-4-(4-methylpiperidin-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(4-methylpiperidin-1-yl)-6-methylpyrimidine 1412954-91-6 C11H17N3O
2-hydroxy-4-(cyclobutyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(cyclobutyl)-6-(tert-butyl)pyrimidine 1412960-51-0 C12H18N2O
2-Hydroxy-4-(n-propyl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(n-propyl)-6-(iso-propyl)pyrimidine 1412958-74-7 C10H16N2O
2-hydroxy-4-(piperidin-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(piperidin-1-yl)-6-(tert-butyl)pyrimidine 1412956-86-5 C13H21N3O
2-Hydroxy-4-(pyrimidin-5-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(pyrimidin-5-yl)-6-(iso-propyl)pyrimidine 1412953-59-3 C11H12N4O
2-hydroxy-4-(pyrrolidin-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(pyrrolidin-1-yl)-6-(tert-butyl)pyrimidine 1412954-56-3 C12H19N3O
2-Hydroxy-4-cyclopropyl-6-(iso-propyl)pyrimidine 2-Hydroxy-4-cyclopropyl-6-(iso-propyl)pyrimidine 1412953-19-5 C10H14N2O
2-Hydroxy-4-morpholino-6-(iso-propyl)pyrimidine 2-Hydroxy-4-morpholino-6-(iso-propyl)pyrimidine 1412961-73-9 C11H17N3O2
2-Methoxy-4-(1H-pyrazol-1-yl)phenylboronic acid pinacol ester 2-Methoxy-4-(1H-pyrazol-1-yl)phenylboronic acid pinacol ester 1562338-80-0 C16H21BN2O3
2-Methyl-5-(iso-propyl)pyridine-3-boronic acid pinacol ester 2-Methyl-5-(iso-propyl)pyridine-3-boronic acid pinacol ester 2223044-65-1 C15H24BNO2
2-Methyl-5-(tert-butyl)pyridine-3-boronic acid pinacol ester 2-Methyl-5-(tert-butyl)pyridine-3-boronic acid pinacol ester 2223032-87-7 C16H26BNO2
2-Methyl-6-(iso-butyl)pyridine-4-boronic acid pinacol ester 2-Methyl-6-(iso-butyl)pyridine-4-boronic acid pinacol ester 2223035-09-2 C16H26BNO2
3-((propan-2-yl-d7)oxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-((propan-2-yl-d7)oxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-22-7 C14H22BNO3
3-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-23-8 C15H24BNO2
3-(3,5-Difluorophenyl)pyridine-2-boronic acid pinacol ester 3-(3,5-Difluorophenyl)pyridine-2-boronic acid pinacol ester 2223042-18-8 C17H18BF2NO2
3-(4-Cyanopyridin-2-yl)phenylboronic acid pinacol ester 3-(4-Cyanopyridin-2-yl)phenylboronic acid pinacol ester 2223049-59-8 C18H19BN2O2
3-(4-Fuoro-2-methylphenyl)pyridine-2-boronic acid pinacol ester 3-(4-Fuoro-2-methylphenyl)pyridine-2-boronic acid pinacol ester 2223053-34-5 C18H21BFNO2
3-(5-Cyanopyridin-2-yl)phenylboronic acid pinacol ester 3-(5-Cyanopyridin-2-yl)phenylboronic acid pinacol ester 2223043-77-2 C18H19BN2O2
3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzonitrile 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzonitrile 2223036-14-2 C18H19BN2O2
3-(iso-Butyl)pyridine-2-boronic acid pinacol ester 3-(iso-Butyl)pyridine-2-boronic acid pinacol ester 2223036-28-8 C15H24BNO2
3-(pyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 3-(pyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 2223048-91-5 C18H19BN2O2
3-(PYRROLIDIN-3-YL)PYRIDINE-5-BORONIC ACID PINACOL ESTER 3-(PYRROLIDIN-3-YL)PYRIDINE-5-BORONIC ACID PINACOL ESTER 1356066-25-5 C15H23BN2O2
3-(tert-Butyl)pyridine-2-boronic acid pinacol ester 3-(tert-Butyl)pyridine-2-boronic acid pinacol ester 2223037-42-9 C15H24BNO2
3,4-DI(PYRIDIN-2-YL)PYRIDINE 3,4-DI(PYRIDIN-2-YL)PYRIDINE 21605-95-8 C15H11N3
3,4-Dibromo-6-cyclobutylpyridine 3,4-Dibromo-6-cyclobutylpyridine 1353855-40-9 C9H9Br2N
3,5-DI(N-BOC-PIPERIDIN-4-YL)PYRIDINE 3,5-DI(N-BOC-PIPERIDIN-4-YL)PYRIDINE 1643563-05-6 C25H39N3O4
3-Amino-6-(2-aminophenyl)pyridazine 3-Amino-6-(2-aminophenyl)pyridazine 1215071-57-0 C10H10N4
3-Amino-6-(2-methylpiperidin-1-yl)pyridazine 3-Amino-6-(2-methylpiperidin-1-yl)pyridazine 1314353-54-2 C10H16N4
3-Amino-6-(cyclobutyl)pyridazine 3-Amino-6-(cyclobutyl)pyridazine 1159816-98-4 C8H11N3
3-Amino-6-(cyclopentyl)pyridine-4-boronic acid pinacol ester 3-Amino-6-(cyclopentyl)pyridine-4-boronic acid pinacol ester 2223045-02-9 C16H25BN2O2
3-Aminopyridazine-4-boronic acid pinacol ester 3-Aminopyridazine-4-boronic acid pinacol ester 2223039-24-3 C10H16BN3O2
3-Bromo-1-(iso-propyl)-1H-pyrrole 3-Bromo-1-(iso-propyl)-1H-pyrrole 1622840-87-2 C7H10BrN
3-Bromo-2-ethylpyridine-4-boronic acid pinacol ester 3-Bromo-2-ethylpyridine-4-boronic acid pinacol ester 2223051-10-1 C13H19BBrNO2
3-Bromo-2-fluoro-6-(iso-propyl)pyridine 3-Bromo-2-fluoro-6-(iso-propyl)pyridine 1622843-16-6 C8H9BrFN
3-bromo-2-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-bromo-2-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223044-66-2 C14H21BBrNO2
3-Bromo-4-(n-propyl)-2-pyridinecarbonitrile 3-Bromo-4-(n-propyl)-2-pyridinecarbonitrile 1622839-77-3 C9H9BrN2
3-Bromo-4-(pyridin-2-yl)-2-pyridinecarbonitrile 3-Bromo-4-(pyridin-2-yl)-2-pyridinecarbonitrile 1622842-69-6 C11H6BrN3
3-Bromo-4-cyclohexyl-2-chloropyridine 3-Bromo-4-cyclohexyl-2-chloropyridine 1622839-25-1 C11H13BrClN
3-Bromo-4-cyclopropyl-2-pyridinecarbonitrile 3-Bromo-4-cyclopropyl-2-pyridinecarbonitrile 1622843-00-8 C9H7BrN2
3-Bromo-6-(2-aminophenyl)pyridazine 3-Bromo-6-(2-aminophenyl)pyridazine 1215071-61-6 C10H8BrN3
3-Bromo-6-(2-methyl-4-fluorophenyl)pyridazine 3-Bromo-6-(2-methyl-4-fluorophenyl)pyridazine 1215074-06-8 C11H8BrFN2
3-Bromo-6-(3-thienyl)pyridazine 3-Bromo-6-(3-thienyl)pyridazine 695184-03-3 C8H5BrN2S
3-Bromo-6-(4-methoxyphenyl)pyridazine 3-Bromo-6-(4-methoxyphenyl)pyridazine 1215073-58-7 C11H9BrN2O
3-Bromo-6-(imidazol-1-yl)pyridazine 3-Bromo-6-(imidazol-1-yl)pyridazine 1159820-70-8 C7H5BrN4
3-Bromo-6-(methylethylamino)pyridazine 3-Bromo-6-(methylethylamino)pyridazine 1027512-99-7 C7H10BrN3
3-Methyl-2-(iso-propyl)pyridine-4-boronic acid pinacol ester 3-Methyl-2-(iso-propyl)pyridine-4-boronic acid pinacol ester 2223044-57-1 C15H24BNO2
3-Methyl-2-cyclopropylpyridine-4-boronic acid pinacol ester 3-Methyl-2-cyclopropylpyridine-4-boronic acid pinacol ester 2223035-17-2 C15H22BNO2
4-(1,4-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(1,4-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222996-35-0 C15H22BNO4
4-(3,4-difluorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(3,4-difluorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223037-91-8 C17H18BF2NO2
4-(3-Thienyl)-1,3,5-triazin-2-amine 4-(3-Thienyl)-1,3,5-triazin-2-amine 1341117-71-2 C7H6N4S
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2-(trifluoromethyl)phenyl)pyridine 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2-(trifluoromethyl)phenyl)pyridine 2223043-35-2 C18H19BF3NO2
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(4-(trifluoromethyl)phenyl)thiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(4-(trifluoromethyl)phenyl)thiazole 1402237-79-9 C16H17BF3NO2S
4-(Cyclohexyl)pyridine-3-boronic acid pinacol ester 4-(Cyclohexyl)pyridine-3-boronic acid pinacol ester 2223043-90-9 C17H26BNO2
4-(Pivaloyloxymethyl)pyridine-2-boronic acid pinacol ester 4-(Pivaloyloxymethyl)pyridine-2-boronic acid pinacol ester 2223045-52-9 C17H26BNO4
4-(tetrahydrofuran-2-yl)aniline 4-(tetrahydrofuran-2-yl)aniline 1267553-72-9 C10H13NO
4,4,5,5-tetramethyl-2-(5-(tetrahydrofuran-2-yl)furan-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(5-(tetrahydrofuran-2-yl)furan-2-yl)-1,3,2-dioxaborolane 2223009-16-1 C14H21BO4
4,4,5,5-tetramethyl-2-(5-propylfuran-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(5-propylfuran-2-yl)-1,3,2-dioxaborolane 2223047-15-0 C13H21BO3
4,6-Dichloro-2-(2-trifluoromethylphenyl)pyrimidine 4,6-Dichloro-2-(2-trifluoromethylphenyl)pyrimidine 1188089-28-2 C11H5Cl2F3N2
4-[(Imidazol-1-yl)sulfonyl]oxypyridine-2-boronic acid pinacol ester 4-[(Imidazol-1-yl)sulfonyl]oxypyridine-2-boronic acid pinacol ester 1402233-97-9 C14H18BN3O5S
4-Amino-2-(2-thienyl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(2-thienyl)pyrimidine-5-boronic acid pinacol ester 2223044-33-3 C14H18BN3O2S
4-Amino-2-(cyclohexyl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(cyclohexyl)pyrimidine-5-boronic acid pinacol ester 2223054-01-9 C16H26BN3O2
4-Amino-2-(iso-propyl)-6-(3-furyl)pyrimidine 4-Amino-2-(iso-propyl)-6-(3-furyl)pyrimidine 1412955-12-4 C11H13N3O
4-Amino-2-cyclopropyl-6-(2-furyl)pyrimidine 4-Amino-2-cyclopropyl-6-(2-furyl)pyrimidine 1249209-51-5 C11H11N3O
4-Amino-2-cyclopropyl-6-(iso-propoxy)pyrimidine 4-Amino-2-cyclopropyl-6-(iso-propoxy)pyrimidine 1412958-69-0 C10H15N3O
4-Amino-2-cyclopropyl-6-(pyrrolidino)pyrimidine 4-Amino-2-cyclopropyl-6-(pyrrolidino)pyrimidine 1412959-90-0 C11H16N4
4-amino-2-methyl-6-(1H-4-methylimidazol-1-yl)pyrimidine 4-amino-2-methyl-6-(1H-4-methylimidazol-1-yl)pyrimidine 1412954-67-6 C9H11N5
4-amino-2-methyl-6-(1H-pyrrol-1-yl)pyrimidine 4-amino-2-methyl-6-(1H-pyrrol-1-yl)pyrimidine 1412954-60-9 C9H10N4
4-Amino-3-(1,4-dioxan-2-yl)pyridine 4-Amino-3-(1,4-dioxan-2-yl)pyridine 1622835-25-9 C9H12N2O2
4-Amino-5-(2-pyridyl)thiazole 4-Amino-5-(2-pyridyl)thiazole 1368541-74-5 C8H7N3S
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