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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
2,4-di(pyridin-2-yl)-6-(pyridin-4-yl)pyrimidine 2,4-di(pyridin-2-yl)-6-(pyridin-4-yl)pyrimidine 2412116-11-9 C19H13N5
2-BROMO-4-(3-METHOXY-PHENYL)-THIAZOLE 2-BROMO-4-(3-METHOXY-PHENYL)-THIAZOLE 412923-56-9 C10H8BrNOS
4-Pyridinamine, N-cyclohexyl-2-fluoro- 4-Pyridinamine, N-cyclohexyl-2-fluoro- 1564591-15-6 C11H15FN2
Pyridine, 4-(3-bromo-1H-pyrazol-1-yl)- Pyridine, 4-(3-bromo-1H-pyrazol-1-yl)- 1874509-70-2 C8H6BrN3
5-Pyrimidinemethanamine, N-(1-ethyl-1H-pyrazol-4-yl)- 5-Pyrimidinemethanamine, N-(1-ethyl-1H-pyrazol-4-yl)- 1339090-16-2 C10H13N5
3-Pyridinecarbonitrile, 5-fluoro-1,2-dihydro-2-oxo- 3-Pyridinecarbonitrile, 5-fluoro-1,2-dihydro-2-oxo- 1506013-17-7 C6H3FN2O
5H-Pyrrolo[3,2-d]pyrimidine-5-carboxylic acid, 2-chloro-, 1,1-dimethylethyl ester 5H-Pyrrolo[3,2-d]pyrimidine-5-carboxylic acid, 2-chloro-, 1,1-dimethylethyl ester 1936241-06-3 C11H12ClN3O2
2H-Benzimidazol-2-one, 5-amino-1,3-dihydro-1,3-dimethyl-6-(3-propoxyphenoxy)- 2H-Benzimidazol-2-one, 5-amino-1,3-dihydro-1,3-dimethyl-6-(3-propoxyphenoxy)- 1800477-35-3 C18H21N3O3
6-azaspiro[3.4]octane-2,5-dione 6-azaspiro[3.4]octane-2,5-dione 2091102-07-5 C7H9NO2
4-Pyridinamine, 2-fluoro-N-(phenylmethyl)- 4-Pyridinamine, 2-fluoro-N-(phenylmethyl)- 1239969-44-8 C12H11FN2
Benzonitrile, 3-(1H-1,2,4-triazol-5-yl)- Benzonitrile, 3-(1H-1,2,4-triazol-5-yl)- 1311314-27-8 C9H6N4
Benzonitrile, 4-(1H-1,2,4-triazol-5-yl)- Benzonitrile, 4-(1H-1,2,4-triazol-5-yl)- 118863-78-8 C9H6N4
1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole 1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole 1088567-34-3 C11H6F6N2
4-CHLORO-1,6-DIMETHYL-1H-IMIDAZO[4,5-C]PYRIDINE 4-CHLORO-1,6-DIMETHYL-1H-IMIDAZO[4,5-C]PYRIDINE 870135-17-4 C8H8ClN3
4-METHYL-6-PYRIDIN-2-YLPYRIMIDIN-2-AMINE 4-METHYL-6-PYRIDIN-2-YLPYRIMIDIN-2-AMINE 91818-70-1 C10H10N4
Temoporfin Temoporfin 122341-38-2 C44H32N4O4
Pyridine, 3-bromo-6-nitro-2-(trifluoromethyl)- Pyridine, 3-bromo-6-nitro-2-(trifluoromethyl)- 1805220-88-5 C6H2BrF3N2O2
Pyridine, 2-(1-cyclohexen-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine, 2-(1-cyclohexen-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1989596-92-0 C17H24BNO2
6-Cyano-5-methoxypyridin-3-ylboronic acid pinacol ester 6-Cyano-5-methoxypyridin-3-ylboronic acid pinacol ester 2304817-18-1 C13H17BN2O3
4-(Methylamino)phenol 4-(Methylamino)phenol 150-75-4 C7H9NO
Etozolin Etozolin 73-09-6 C13H20N2O3S
1-allyl-2-methyl-5-nitro-1H-imidazole 1-allyl-2-methyl-5-nitro-1H-imidazole 13230-43-8 C7H9N3O2
2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (4S)- 2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (4S)- 23224-65-9 C12H11NO5
Pyridine, 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl]- Pyridine, 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl]- 1606122-05-7 C14H18BN3O2
1,3-dimethylpyrrolidine-2,5-dione 1,3-dimethylpyrrolidine-2,5-dione 15542-96-8 C6H9NO2
2-Methyl-4-nitro-6-(trifluoromethyl)pyridine 2-Methyl-4-nitro-6-(trifluoromethyl)pyridine 2055275-03-9 C7H5F3N2O2
3-bromo-4-cyclopropyl-4H-1,2,4-triazole 3-bromo-4-cyclopropyl-4H-1,2,4-triazole 2168765-04-4 C5H6BrN3
4-(Tetrahydropyran-4-yl)pyridine-2-boronic acid pinacol ester 4-(Tetrahydropyran-4-yl)pyridine-2-boronic acid pinacol ester 1402166-21-5 C16H24BNO3
1,3-dihydro-1-[1-benzyl-4-piperidinyl]-2H-benzimidazol-2-one 1,3-dihydro-1-[1-benzyl-4-piperidinyl]-2H-benzimidazol-2-one 16148-06-4 C19H21N3O
2,5-dimethylpyrrolidine-1-propanol 2,5-dimethylpyrrolidine-1-propanol 1904-16-1 C9H19NO
2-(2-phenylethyl)pyridine 2-(2-phenylethyl)pyridine 2116-62-3 C13H13N
1-(4-methylpyrimidin-2-yl)ethan-1-one 1-(4-methylpyrimidin-2-yl)ethan-1-one 71850-85-6 C7H8N2O
(R)-3-(pyrrolidin-2-yl)pyridine (R)-3-(pyrrolidin-2-yl)pyridine 7076-23-5 C9H12N2
2-azido-1H-benzimidazole 2-azido-1H-benzimidazole 1516-74-1 C7H5N5
1-Azetidinecarboxylic acid, 3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]-, 1,1-dimethylethyl ester 1-Azetidinecarboxylic acid, 3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]-, 1,1-dimethylethyl ester 2223011-78-5 C19H29BN2O4
(S)-1-Boc-3-hydroxymethyl-piperazine (S)-1-Boc-3-hydroxymethyl-piperazine 314741-40-7 C10H20N2O3
1,?4-?Benzenedicarboxylic acid, 2,?5-?di-?1H-?imidazol-?1-?yl-?, 1,?4-?diethyl ester 1,?4-?Benzenedicarboxylic acid, 2,?5-?di-?1H-?imidazol-?1-?yl-?, 1,?4-?diethyl ester 1942879-47-1 C18H18N4O4
3-Methyl-6-phenylimidazo[2,1-b][1,3]thiazol-5-amine 3-Methyl-6-phenylimidazo[2,1-b][1,3]thiazol-5-amine 94802-79-6 C12H11N3S
6-Methoxy-1H-indazole 6-Methoxy-1H-indazole 3522-07-4 C8H8N2O
Pyrazolo[1,5-a]pyridine-3-carbonitrile, 7-bromo- Pyrazolo[1,5-a]pyridine-3-carbonitrile, 7-bromo- 1824091-22-6 C8H4BrN3
Pyridine, 2-[(4S)-4-(1,1-dimethylethyl)-4,5-dihydro-1-phenyl-1H-imidazol-2-yl]- Pyridine, 2-[(4S)-4-(1,1-dimethylethyl)-4,5-dihydro-1-phenyl-1H-imidazol-2-yl]- 2688032-35-9 C18H21N3
4H-1,2,4-Triazole, 3-bromo-4-(4-methoxyphenyl)- 4H-1,2,4-Triazole, 3-bromo-4-(4-methoxyphenyl)- 2460491-73-8 C9H8BrN3O
4-Pyridin-2,3,5,6-d4-ol (8CI) 4-Pyridin-2,3,5,6-d4-ol (8CI) 25813-18-7 C5H5NO
Pyridine, 3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]- Pyridine, 3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]- 1286202-08-1 C14H18BN3O2
Ethyl 1H-indole-6-carboxylate Ethyl 1H-indole-6-carboxylate 50820-64-9 C11H11NO2
5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE 5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE 4943-67-3 C8H8N2
2',5'-bis((1H-imidazol-1-yl)methyl)-[1,1':4',1''-terphenyl]-4,4''-dicarbaldehyde 2',5'-bis((1H-imidazol-1-yl)methyl)-[1,1':4',1''-terphenyl]-4,4''-dicarbaldehyde 2375720-19-5 C28H22N4O2
Oxazole, 4-bromo-2-(1-methylethyl)- Oxazole, 4-bromo-2-(1-methylethyl)- 2697156-72-0 C6H8BrNO
Imidazo[1,5-a]pyridin-8-amine (9CI) Imidazo[1,5-a]pyridin-8-amine (9CI) 697739-15-4 C7H7N3
4H-1,2,4-Triazole, 3-bromo-4-propyl- 4H-1,2,4-Triazole, 3-bromo-4-propyl- 2460491-54-5 C5H8BrN3
Pyridine, 4-fluoro-2-(phenylmethoxy)- Pyridine, 4-fluoro-2-(phenylmethoxy)- 2155854-88-7 C12H10FNO
Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) 56267-48-2 C9H13NO3
Pyrimidine, 4-(4-bromophenyl)- (9CI) Pyrimidine, 4-(4-bromophenyl)- (9CI) 53975-33-0 C10H7BrN2
1H-1,2,3-Triazole, 5-bromo-1-(2-methylpropyl)- 1H-1,2,3-Triazole, 5-bromo-1-(2-methylpropyl)- 1393559-99-3 C6H10BrN3
3-(1H-Imidazol-4-yl)pyridine 3-(1H-Imidazol-4-yl)pyridine 51746-85-1 C8H7N3
Pyrido[2,3-d]pyrimidin-4(3H)-one, 6-bromo-2,7-dimethyl- Pyrido[2,3-d]pyrimidin-4(3H)-one, 6-bromo-2,7-dimethyl- 2090991-89-0 C9H8BrN3O
1-(3,4-Dimethylphenyl)piperazine 1-(3,4-Dimethylphenyl)piperazine 1014-05-7 C12H18N2
9H-Carbazole, 2-[3-(1H-benzimidazol-1-yl)phenoxy]-9-[4-(1,1-dimethylethyl)-2-pyridinyl]- 9H-Carbazole, 2-[3-(1H-benzimidazol-1-yl)phenoxy]-9-[4-(1,1-dimethylethyl)-2-pyridinyl]- 2264042-89-7 C34H28N4O
2-Chloro-4-(4-trifluoromethyl-phenyl)-pyrimidine 2-Chloro-4-(4-trifluoromethyl-phenyl)-pyrimidine 659729-15-4 C11H6ClF3N2
2-Chloro-4-(4-fluoro-2-methyl-phenyl)-pyrimidine 2-Chloro-4-(4-fluoro-2-methyl-phenyl)-pyrimidine 954235-06-4 C11H8ClFN2
2,4(3H,5H)-Pyrimidinedione, 6-amino- (9CI) 2,4(3H,5H)-Pyrimidinedione, 6-amino- (9CI) 14436-34-1 C4H5N3O2
2-Oxa-8-azaspiro[4.5]decan-4-ol (9CI) 2-Oxa-8-azaspiro[4.5]decan-4-ol (9CI) 777049-50-0 C8H15NO2
4-(1H-Benzoimidazol-2-yl)-benzoic acid 4-(1H-Benzoimidazol-2-yl)-benzoic acid 66631-29-6 C14H10N2O2
4-AMINODIBENZOFURAN 4-AMINODIBENZOFURAN 50548-43-1 C12H9NO
2-(3-METHOXYPHENYL)PYRROLIDINE 2-(3-METHOXYPHENYL)PYRROLIDINE 103861-77-4 C11H15NO
ETHYL 2-[BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONO] PROPIONATE ETHYL 2-[BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONO] PROPIONATE 107905-52-2 C9H13F6O5P
Tolazoline Tolazoline C10H12N2
Pyridine, 5-bromo-2-cyclopropyl-4-nitro- Pyridine, 5-bromo-2-cyclopropyl-4-nitro- 2460501-23-7 C8H7BrN2O2
Piperazine, 1,4-bis(3-chloropropyl)- Piperazine, 1,4-bis(3-chloropropyl)- 27145-02-4 C10H20Cl2N2
4,5,6,7-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridine 4,5,6,7-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridine 109904-25-8 C26H23NS
[2,2'-Bipyridin]-6-amine, 6'-bromo- [2,2'-Bipyridin]-6-amine, 6'-bromo- 177087-59-1 C10H8BrN3
Imidazo[1,5-a]quinoline, 1-phenyl- Imidazo[1,5-a]quinoline, 1-phenyl- 148149-24-0 C17H12N2
Oxazole, 4-bromo-2-methoxy- Oxazole, 4-bromo-2-methoxy- 1890586-59-0 C4H4BrNO2
2,3-difluoropyridine-4,5,6-d3 2,3-difluoropyridine-4,5,6-d3 2363782-20-9 C5D3F2N
Pyridine, 3-(1-methylpropyl)- Pyridine, 3-(1-methylpropyl)- 25224-14-0 C9H13N
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3,4,6-d3-2-amine 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3,4,6-d3-2-amine 2819702-23-1
5-(methyl-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(methyl-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2819702-40-2 C12H18BNO2
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine-3,4,6-d3 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine-3,4,6-d3 2819702-85-5 C12H15BF3NO2
2-(methyl-d3)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(methyl-d3)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2819702-98-0 C12H18BNO2
tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate 2819703-34-7 C21H33BN2O4
tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2819703-47-2 C21H33BN2O4
2-chloro-4,6-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-chloro-4,6-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2819706-51-7 C10H12BClF2N2O2
methyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline-5-carboxylate methyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline-5-carboxylate 2819706-62-0 C16H19BN2O4
3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)tetrahydro-4H-pyran-4-one 3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)tetrahydro-4H-pyran-4-one 2819707-17-8 C16H22BNO4
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazine-3,5,6-d3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazine-3,5,6-d3 2819705-21-8 C10H15BN2O2
2-(5-cyclopropyl-2-methoxy-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(5-cyclopropyl-2-methoxy-4-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2819707-55-4 C17H22BF3O3
2(1H)-Pyridinone, 4-bromo-3-cyclopropyl- 2(1H)-Pyridinone, 4-bromo-3-cyclopropyl- 1822637-04-6 C8H8BrNO
[2,2'-Bipyridine]-5,6'-dicarbonitrile [2,2'-Bipyridine]-5,6'-dicarbonitrile 1185316-45-3 C12H6N4
2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis(3-methylphenyl)-, (4S,4'S)- 2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis(3-methylphenyl)-, (4S,4'S)- 2567868-02-2 C20H20N2O2
Pyridine, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiazolyl]- Pyridine, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiazolyl]- 1402165-93-8 C14H17BN2O2S
Pentonic acid, 2,5-dideoxy-3-C-methyl-, γ-lactone, 3-(2-methyl-2-propenoate) Pentonic acid, 2,5-dideoxy-3-C-methyl-, γ-lactone, 3-(2-methyl-2-propenoate) 324761-25-3 C10H14O4
3-Pyridinamine, N-methyl-2-nitro- 3-Pyridinamine, N-methyl-2-nitro- 32605-06-4 C6H7N3O2
4-Bromo-9H-fluoren-9-one 4-Bromo-9H-fluoren-9-one 4269-17-4 C13H7BrO
1H-1,2,3-Triazole,4-(2-methoxyphenyl)-(9CI) 1H-1,2,3-Triazole,4-(2-methoxyphenyl)-(9CI) 369363-77-9 C9H9N3O
2-Pyridinecarboxamide,N-3-pyridinyl-(9CI) 2-Pyridinecarboxamide,N-3-pyridinyl-(9CI) 184870-10-8 C11H9N3O
1-Piperidinecarboxylic acid, 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinyl-4,6-d2]-, 1,1-dimethylethyl ester 1-Piperidinecarboxylic acid, 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinyl-4,6-d2]-, 1,1-dimethylethyl ester 2710294-97-4 C20H32BN3O4
2-chloro-4-fluoropyrimidine-5,6-d2 2-chloro-4-fluoropyrimidine-5,6-d2 2363789-37-9 C4ClD2FN2
Pyridine-2,3,4,5-d4, 6-methyl- (9CI) Pyridine-2,3,4,5-d4, 6-methyl- (9CI) 102064-44-8 C6H7N
2-Pyridinamine,4-(1-piperazinyl)-(9CI) 2-Pyridinamine,4-(1-piperazinyl)-(9CI) 470442-95-6 C9H14N4
1H-Pyrazole-4-carbonitrile,1,3-dimethyl-(9CI) 1H-Pyrazole-4-carbonitrile,1,3-dimethyl-(9CI) 87412-96-2 C6H7N3
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