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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
3-bromo-5-(4-methylpiperidin-1-yl)pyridine-2,4,6-d3 3-bromo-5-(4-methylpiperidin-1-yl)pyridine-2,4,6-d3 2363781-44-4 C11H12BrD3N2
6-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridin-3-amine 6-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridin-3-amine 2363785-23-1 C11H5D12N3
5-bromo-2-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridine-3,4,6-d3 5-bromo-2-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridine-3,4,6-d3 2363786-49-4 C11BrD15N2
5-(2-methylpiperidin-1-yl)pyridin-3,4,6-d3-2-amine 5-(2-methylpiperidin-1-yl)pyridin-3,4,6-d3-2-amine 2363781-55-7 C11H14D3N3
3-bromo-4-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridine 3-bromo-4-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridine 2363779-95-5 C11H3BrD12N2
4-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridin-2,5,6-d3-3-amine 4-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridin-2,5,6-d3-3-amine 2363779-72-8 C11H2D15N3
3-bromo-6-(2-methylpiperidin-1-yl)pyridazine-4,5-d2 3-bromo-6-(2-methylpiperidin-1-yl)pyridazine-4,5-d2 2363782-18-5 C10H12BrD2N3
6-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridazin-4,5-d2-3-ol 6-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridazin-4,5-d2-3-ol 2363781-51-3 C10HD14N3O
6-(4-methylpiperidin-1-yl)pyridazin-4,5-d2-3-ol 6-(4-methylpiperidin-1-yl)pyridazin-4,5-d2-3-ol 2363780-43-0 C10H13D2N3O
4-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyrimidin-2-amine 4-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyrimidin-2-amine 2363785-76-4 C10H4D12N4
4-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyrimidin-5,6-d2-2-ol 4-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyrimidin-5,6-d2-2-ol 2363786-54-1 C10HD14N3O
4-(4-methylpiperidin-1-yl)pyrimidin-5,6-d2-2-amine 4-(4-methylpiperidin-1-yl)pyrimidin-5,6-d2-2-amine 2363789-08-4 C10H14D2N4
5-bromo-2-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyrimidine-4,6-d2 5-bromo-2-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyrimidine-4,6-d2 2363783-82-6 C10BrD14N3
2-(4-methylpiperidin-1-yl)pyrimidin-4,6-d2-5-amine 2-(4-methylpiperidin-1-yl)pyrimidin-4,6-d2-5-amine 2363785-94-6 C10H14D2N4
2-(tert-butoxy)-4-fluoropyridine-3,5,6-d3 2-(tert-butoxy)-4-fluoropyridine-3,5,6-d3 2363789-89-1 C9H9D3FNO
2,3-dichloropyridine-4,5,6-d3 2,3-dichloropyridine-4,5,6-d3 1001003-85-5 C5Cl2D3N
3,4-dibromopyridine-2,5,6-d3 3,4-dibromopyridine-2,5,6-d3 2363787-54-4 C5Br2D3N
2,6-dibromo-4-chloropyridine-3,5-d2 2,6-dibromo-4-chloropyridine-3,5-d2 2460500-99-4 C5Br2ClD2N
3-bromo-5-(1H-imidazol-2-yl-4,5-d2)pyridine-2,4,6-d3 3-bromo-5-(1H-imidazol-2-yl-4,5-d2)pyridine-2,4,6-d3 2256713-79-6 C8HBrD5N3
2-bromo-6-(1H-imidazol-2-yl-4,5-d2)pyridine-3,4,5-d3 2-bromo-6-(1H-imidazol-2-yl-4,5-d2)pyridine-3,4,5-d3 2256713-81-0 C8HBrD5N3
2-bromo-4-chloro-6-(trifluoromethyl)pyridine-3,5-d2 2-bromo-4-chloro-6-(trifluoromethyl)pyridine-3,5-d2 2460490-52-0 C6BrClD2F3N
2-bromo-5-(1H-imidazol-2-yl-4,5-d2)pyridine 2-bromo-5-(1H-imidazol-2-yl-4,5-d2)pyridine 2256713-86-5 C8H4BrD2N3
2,4-dibromo-6-(trifluoromethyl)pyridine-3,5-d2 2,4-dibromo-6-(trifluoromethyl)pyridine-3,5-d2 2460492-51-5 C6Br2D2F3N
6-bromo-4-chloropyridin-3,5-d2-2-amine 6-bromo-4-chloropyridin-3,5-d2-2-amine 2460492-56-0 C5H2BrClD2N2
2,4-dibromo-6-(methyl-d3)pyridine-3,5-d2 2,4-dibromo-6-(methyl-d3)pyridine-3,5-d2 2363787-15-7 C6Br2D5N
3-(methyl-d3)pyridin-2,5,6-d3-4-ol 3-(methyl-d3)pyridin-2,5,6-d3-4-ol 2460490-88-2 C6HD6NO
3,4-bis(methyl-d3)pyridin-5,6-d2-2-amine 3,4-bis(methyl-d3)pyridin-5,6-d2-2-amine 2460490-92-8 C7H2D8N2
2-bromo-4-(1H-imidazol-2-yl-4,5-d2)pyrimidine 2-bromo-4-(1H-imidazol-2-yl-4,5-d2)pyrimidine 2256714-01-7 C7H3BrD2N4
3,5-dibromo-2-(methyl-d3)pyridine-4,6-d2 3,5-dibromo-2-(methyl-d3)pyridine-4,6-d2 2600399-95-7 C6Br2D5N
5-bromo-2-(cyclopropyl-d5)pyridine 5-bromo-2-(cyclopropyl-d5)pyridine 2600399-37-7 C8H3BrD5N
2-(cyclopropyl-d5)pyridin-4-ol 2-(cyclopropyl-d5)pyridin-4-ol 2600400-40-4 C8H4D5NO
5-(cyclopropyl-d5)pyridin-3,4,6-d3-2-ol 5-(cyclopropyl-d5)pyridin-3,4,6-d3-2-ol 2600398-86-3 C8HD8NO
6-(cyclopropyl-d5)pyridin-3,4,5-d3-2-amine 6-(cyclopropyl-d5)pyridin-3,4,5-d3-2-amine 2600399-86-6 C8H2D8N2
2-(cyclopropyl-d5)pyrimidin-5,6-d2-4-amine 2-(cyclopropyl-d5)pyrimidin-5,6-d2-4-amine 2600399-81-1 C7H2D7N3
2,6-dibromopyridin-3,5-d2-4-amine 2,6-dibromopyridin-3,5-d2-4-amine 2600399-85-5 C5H2Br2D2N2
imidazo[1,2-a]pyridin-6,7,8-d3-5-ol imidazo[1,2-a]pyridin-6,7,8-d3-5-ol 2645412-84-4 C7H3D3N2O
2,8-dimethylimidazo[1,2-b]pyridazin-3,7-d2-6-ol 2,8-dimethylimidazo[1,2-b]pyridazin-3,7-d2-6-ol 2645419-90-3 C8H7D2N3O
imidazo[1,2-b]pyridazin-d4-6-amine imidazo[1,2-b]pyridazin-d4-6-amine 2645415-87-6 C6H2D4N4
1-(4,6-dibromopyridin-2-yl-3,5-d2)ethan-1-one-2,2,2-d3 1-(4,6-dibromopyridin-2-yl-3,5-d2)ethan-1-one-2,2,2-d3 2645412-04-8 C7Br2D5NO
2,4,6-trifluoropyridine-3,5-d2 2,4,6-trifluoropyridine-3,5-d2 2645419-92-5 C5D2F3N
6-amino-4-bromopyridin-2,5-d2-3-ol 6-amino-4-bromopyridin-2,5-d2-3-ol 2645413-35-8 C5H3BrD2N2O
2-amino-3-bromopyridin-5,6-d2-4-ol 2-amino-3-bromopyridin-5,6-d2-4-ol 2645412-55-9 C5H3BrD2N2O
3-bromo-2-fluoro-4-(methoxy-d3)pyridine-5,6-d2 3-bromo-2-fluoro-4-(methoxy-d3)pyridine-5,6-d2 2645417-29-2 C6BrD5FNO
2-(methyl-d3)pyridin-3,5,6-d3-4-ol 2-(methyl-d3)pyridin-3,5,6-d3-4-ol 2645413-50-7 C6HD6NO
2-(methyl-d3)pyrimidin-4(3H)-one 2-(methyl-d3)pyrimidin-4(3H)-one 2172151-98-1 C5H3D3N2O
6-(methyl-d3)pyrimidin-4-amine 6-(methyl-d3)pyrimidin-4-amine 2182195-57-7 C5H4D3N3
2-chloro-4-(methyl-d3)-5-(trifluoromethyl)pyrimidine 2-chloro-4-(methyl-d3)-5-(trifluoromethyl)pyrimidine 2645419-99-2 C6HClD3F3N2
6-bromo-1-(methyl-d3)pyridin-2(1H)-one-3,4,5-d3 6-bromo-1-(methyl-d3)pyridin-2(1H)-one-3,4,5-d3 2645417-41-8 C6BrD6NO
3,5-bis(methyl-d3)-2-(trifluoromethyl)pyridin-6-d-4-amine 3,5-bis(methyl-d3)-2-(trifluoromethyl)pyridin-6-d-4-amine 2645417-47-4 C8H2D7F3N2
2-fluoro-3-(methyl-d3)pyridin-5,6-d2-4-amine 2-fluoro-3-(methyl-d3)pyridin-5,6-d2-4-amine 2645413-71-2 C6H2D5FN2
2,6-bis(methyl-d3)pyridin-3,5-d2-4-ol 2,6-bis(methyl-d3)pyridin-3,5-d2-4-ol 2645418-50-2 C7HD8NO
2-((azetidin-3-yl-2,2,3,4,4-d5)oxy)-5-bromopyridine-3,4,6-d3 2-((azetidin-3-yl-2,2,3,4,4-d5)oxy)-5-bromopyridine-3,4,6-d3 2645417-44-1 C8HBrD8N2O
2-bromo-5-(2-(methoxy-d3)ethoxy-1,1,2,2-d4)pyridine-3,4,6-d3 2-bromo-5-(2-(methoxy-d3)ethoxy-1,1,2,2-d4)pyridine-3,4,6-d3 2645418-78-4 C8BrD10NO2
4-bromo-2-((methoxy-d3)methyl-d2)pyridine 4-bromo-2-((methoxy-d3)methyl-d2)pyridine 2645412-62-8 C7H3BrD5NO
2-bromo-4-((methoxy-d3)methyl-d2)pyridine 2-bromo-4-((methoxy-d3)methyl-d2)pyridine 2645413-90-5 C7H3BrD5NO
6-((methoxy-d3)methyl-d2)pyridin-3,4,5-d3-2-amine 6-((methoxy-d3)methyl-d2)pyridin-3,4,5-d3-2-amine 2645413-91-6 C7H2D8N2O
2-((methoxy-d3)methyl-d2)pyrimidin-5,6-d2-4-amine 2-((methoxy-d3)methyl-d2)pyrimidin-5,6-d2-4-amine 2645420-04-6 C6H2D7N3O
5-bromo-7-(methyl-d3)pyrazolo[1,5-a]pyrimidine-2,3,6-d3 5-bromo-7-(methyl-d3)pyrazolo[1,5-a]pyrimidine-2,3,6-d3 2645412-79-7 C7BrD6N3
8-bromoimidazo[1,2-a]pyridine-2,3,5,6,7-d5 8-bromoimidazo[1,2-a]pyridine-2,3,5,6,7-d5 2645412-90-2 C7BrD5N2
imidazo[1,5-a]pyridin-d5-5-amine imidazo[1,5-a]pyridin-d5-5-amine 2645411-82-9 C7H2D5N3
5-methylpyridin-2,4,6-d3-3-ol 5-methylpyridin-2,4,6-d3-3-ol 2645415-79-6 C6H4D3NO
4-methylpyridin-3,5,6-d3-2-amine 4-methylpyridin-3,5,6-d3-2-amine 2645415-85-4 C6H5D3N2
5-bromo-N-methylpyridin-3,4,6-d3-2-amine 5-bromo-N-methylpyridin-3,4,6-d3-2-amine 2645416-11-9 C6H4BrD3N2
2-bromo-N-methylpyridin-3,5,6-d3-4-amine 2-bromo-N-methylpyridin-3,5,6-d3-4-amine 2645415-88-7 C6H4BrD3N2
2-bromo-6-fluoro-4-methoxypyridine-3,5-d2 2-bromo-6-fluoro-4-methoxypyridine-3,5-d2 2645413-57-4 C6H3BrD2FNO
tert-butyl 4-(4-hydroxypyridin-2-yl-3,5,6-d3)piperazine-1-carboxylate tert-butyl 4-(4-hydroxypyridin-2-yl-3,5,6-d3)piperazine-1-carboxylate 2645416-91-5 C14H18D3N3O3
3-bromo-2-(methyl-d3)pyridin-4-amine 3-bromo-2-(methyl-d3)pyridin-4-amine 2697156-19-5 C6H4BrD3N2
hexahydropyrimidine-2,2,4,4,5,5,6,6-d8 hexahydropyrimidine-2,2,4,4,5,5,6,6-d8 2697162-40-4 C4H2D8N2
tert-butyl 4-(5-bromopyridin-3-yl)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 tert-butyl 4-(5-bromopyridin-3-yl)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 2697155-40-9 C15H12BrD9N2O2
tert-butyl 4-(2-bromopyrimidin-4-yl-5,6-d2)piperidine-1-carboxylate tert-butyl 4-(2-bromopyrimidin-4-yl-5,6-d2)piperidine-1-carboxylate 2697162-49-3 C14H18BrD2N3O2
tert-butyl 4-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 tert-butyl 4-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 2697155-97-6 C15H9BrD12N2O2
2-bromo-6-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 2-bromo-6-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 2697162-52-8 C10H7BrD5NO
2-bromo-4-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine-3,5,6-d3 2-bromo-4-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine-3,5,6-d3 2697155-77-2 C10H4BrD8NO
2-bromo-4-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyrimidine 2-bromo-4-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyrimidine 2697155-81-8 C9H6BrD5N2O
5-bromo-2,4-bis(methyl-d3)pyrimidine-6-d 5-bromo-2,4-bis(methyl-d3)pyrimidine-6-d 2697156-10-6 C6BrD7N2
2-(1-bromoethyl-1,2,2,2-d4)pyridine 2-(1-bromoethyl-1,2,2,2-d4)pyridine 2697144-33-3 C7H4BrD4N
5-(trifluoromethyl)pyridin-2,4,6-d3-3-amine 5-(trifluoromethyl)pyridin-2,4,6-d3-3-amine 2697162-91-5 C6H2D3F3N2
2-ethyl-4-fluoropyridine-3,5,6-d3 2-ethyl-4-fluoropyridine-3,5,6-d3 2697156-43-5 C7H5D3FN
2-(ethyl-d5)-5-fluoropyridine 2-(ethyl-d5)-5-fluoropyridine 2697155-82-9 C7H3D5FN
4-bromo-3,5-bis(methyl-d3)pyridine 4-bromo-3,5-bis(methyl-d3)pyridine 2697155-89-6 C7H2BrD6N
methyl 1-(methyl-d3)-1,2,3,6-tetrahydropyridine-4-carboxylate methyl 1-(methyl-d3)-1,2,3,6-tetrahydropyridine-4-carboxylate 2697162-68-6 C8H10D3NO2
2,4-dibromo-3-(methoxy-d3)pyridine-5,6-d2 2,4-dibromo-3-(methoxy-d3)pyridine-5,6-d2 2697156-16-2 C6Br2D5NO
2,4-dibromo-5-methoxypyridine-3,6-d2 2,4-dibromo-5-methoxypyridine-3,6-d2 2697162-72-2 C6H3Br2D2NO
2-(difluoromethyl)-5-(methoxy-d3)pyridin-4,6-d2-3-amine 2-(difluoromethyl)-5-(methoxy-d3)pyridin-4,6-d2-3-amine 2711075-19-1 C7H3D5F2N2O
5'-bromo-[2,2'-bipyridin]-3,3',4,4',6,6'-d6-5-amine 5'-bromo-[2,2'-bipyridin]-3,3',4,4',6,6'-d6-5-amine 2711075-30-6 C10H2BrD6N3
4-chloropyridin-2,5,6-d3-3-ol 4-chloropyridin-2,5,6-d3-3-ol 2710298-95-4 C5HClD3NO
3-(trifluoromethyl)pyridin-4,5,6-d3-2-amine 3-(trifluoromethyl)pyridin-4,5,6-d3-2-amine 2768654-80-2 C6H2D3F3N2
3-methylpyridine-2,4,5,6-d4 3-methylpyridine-2,4,5,6-d4 135742-46-0 C6H3D4N
tert-butyl 3-(2-bromopyridin-4-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(2-bromopyridin-4-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768654-54-0 C15H12BrD9N2O2
tert-butyl 3-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate tert-butyl 3-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate 2768657-43-6 C15H18BrD3N2O2
tert-butyl 3-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-bromopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768654-68-6 C15H9BrD12N2O2
tert-butyl 3-(6-aminopyridin-2-yl-3,4,5-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(6-aminopyridin-2-yl-3,4,5-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768657-30-1 C15H11D12N3O2
5-bromo-3-(methyl-d3)pyridin-4,6-d2-2-amine 5-bromo-3-(methyl-d3)pyridin-4,6-d2-2-amine 2256740-07-3 C6H2BrD5N2
3,4-dibromo-2-fluoropyridine-5,6-d2 3,4-dibromo-2-fluoropyridine-5,6-d2 2768655-62-3 C5Br2D2FN
3-chloro-4-(methyl-d3)pyridin-5,6-d2-2-ol 3-chloro-4-(methyl-d3)pyridin-5,6-d2-2-ol 2768654-90-4 C6HClD5NO
2-chloro-6-methoxypyridin-3,5-d2-4-amine 2-chloro-6-methoxypyridin-3,5-d2-4-amine 2806719-42-4 C6H5ClD2N2O
4-chloro-3-cyclopropyl-2-(methyl-d3)pyridine 4-chloro-3-cyclopropyl-2-(methyl-d3)pyridine 2806728-73-2 C9H7ClD3N
4-bromo-6-(methyl-d3)pyridin-2,5-d2-3-ol 4-bromo-6-(methyl-d3)pyridin-2,5-d2-3-ol 2806719-13-9 C6HBrD5NO
2-chloro-5-methylpyridin-3,6-d2-4-amine 2-chloro-5-methylpyridin-3,6-d2-4-amine 2806720-47-6 C6H5ClD2N2
5-bromo-2-chloropyridin-3,6-d2-4-amine 5-bromo-2-chloropyridin-3,6-d2-4-amine 2806719-21-9 C5H2BrClD2N2
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