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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
5-bromo-2-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridine 5-bromo-2-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridine 2363780-93-0 C11H3BrD12N2
6-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridin-2,4,5-d3-3-amine 6-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridin-2,4,5-d3-3-amine 2363786-08-5 C11H2D15N3
2-bromo-5-(2-methylpiperidin-1-yl)pyridine-3,4,6-d3 2-bromo-5-(2-methylpiperidin-1-yl)pyridine-3,4,6-d3 2363783-25-7 C11H12BrD3N2
5-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyridin-2-amine 5-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyridin-2-amine 2363785-33-3 C11H5D12N3
2-bromo-5-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridine 2-bromo-5-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyridine 2363786-20-1 C11H3BrD12N2
4-(3-methylpiperidin-1-yl)pyridin-2,5,6-d3-3-amine 4-(3-methylpiperidin-1-yl)pyridin-2,5,6-d3-3-amine 2363781-26-2 C11H14D3N3
4-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridin-3-amine 4-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyridin-3-amine 2363788-64-9 C11H5D12N3
3-bromo-6-(3-methylpiperidin-1-yl)pyridazine-4,5-d2 3-bromo-6-(3-methylpiperidin-1-yl)pyridazine-4,5-d2 2363789-81-3 C10H12BrD2N3
6-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyridazin-4,5-d2-3-ol 6-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyridazin-4,5-d2-3-ol 2363782-22-1 C10HD14N3O
4-(2-methylpiperidin-1-yl)pyrimidin-5,6-d2-2-ol 4-(2-methylpiperidin-1-yl)pyrimidin-5,6-d2-2-ol 2363787-01-1 C10H13D2N3O
4-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyrimidin-2-ol 4-(3-(methyl-d3)piperidin-1-yl-2,2,3,4,4,5,5,6,6-d9)pyrimidin-2-ol 2363789-09-5 C10H3D12N3O
4-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyrimidin-5,6-d2-2-ol 4-(4-(methyl-d3)piperidin-1-yl-2,2,3,3,4,5,5,6,6-d9)pyrimidin-5,6-d2-2-ol 2363789-84-6 C10HD14N3O
5-bromo-2-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyrimidine-4,6-d2 5-bromo-2-(2-(methyl-d3)piperidin-1-yl-2,3,3,4,4,5,5,6,6-d9)pyrimidine-4,6-d2 2363786-56-3 C10BrD14N3
2,4,6-tribromopyridine-3,5-d2 2,4,6-tribromopyridine-3,5-d2 2363782-53-8 C5Br3D2N
2,4-difluoropyrimidine-5,6-d2 2,4-difluoropyrimidine-5,6-d2 2363786-98-3 C4D2F2N2
2-fluoropyrimidine-4,5,6-d3 2-fluoropyrimidine-4,5,6-d3 2363789-29-9 C4D3FN2
3-bromo-4-(methyl-d3)pyridine-2,5,6-d3 3-bromo-4-(methyl-d3)pyridine-2,5,6-d3 2363785-53-7 C6BrD6N
3-fluoro-4-methylpyridine-2,5,6-d3 3-fluoro-4-methylpyridine-2,5,6-d3 2363789-92-6 C6H3D3FN
3,5-dibromo-2-chloropyridine-4,6-d2 3,5-dibromo-2-chloropyridine-4,6-d2 2460493-01-8 C5Br2ClD2N
2-bromo-6-(1H-imidazol-2-yl-4,5-d2)pyridine 2-bromo-6-(1H-imidazol-2-yl-4,5-d2)pyridine 2256713-80-9 C8H4BrD2N3
2,6-dibromo-4-methoxypyridine-3,5-d2 2,6-dibromo-4-methoxypyridine-3,5-d2 2460493-48-3 C6H3Br2D2NO
4-bromo-2-(1H-imidazol-2-yl-4,5-d2)pyridine-3,5,6-d3 4-bromo-2-(1H-imidazol-2-yl-4,5-d2)pyridine-3,5,6-d3 2256713-83-2 C8HBrD5N3
2,6-dichloro-4-(trifluoromethyl)pyridine-3,5-d2 2,6-dichloro-4-(trifluoromethyl)pyridine-3,5-d2 2460490-57-5 C6Cl2D2F3N
2-bromo-4-(1H-imidazol-2-yl-4,5-d2)pyridine 2-bromo-4-(1H-imidazol-2-yl-4,5-d2)pyridine 2256713-89-8 C8H4BrD2N3
2-bromo-4,5-bis(methyl-d3)pyridine 2-bromo-4,5-bis(methyl-d3)pyridine 2259751-85-2 C7H2BrD6N
4-bromo-2,5-bis(methyl-d3)pyridine-3,6-d2 4-bromo-2,5-bis(methyl-d3)pyridine-3,6-d2 2460490-23-5 C7BrD8N
4-chloro-3,5-bis(methyl-d3)pyridine-2,6-d2 4-chloro-3,5-bis(methyl-d3)pyridine-2,6-d2 2460493-31-4 C7ClD8N
6-hydroxypyrimidin-4(3H)-one-2,5-d2 6-hydroxypyrimidin-4(3H)-one-2,5-d2 2600399-97-9 C4H2D2N2O2
2-bromo-5-(cyclopropyl-d5)pyridine 2-bromo-5-(cyclopropyl-d5)pyridine 2600399-44-6 C8H3BrD5N
4-(cyclopropyl-d5)pyridin-2-ol 4-(cyclopropyl-d5)pyridin-2-ol 2600400-62-0 C8H4D5NO
6-(cyclopropyl-d5)pyridin-2,4,5-d3-3-amine 6-(cyclopropyl-d5)pyridin-2,4,5-d3-3-amine 2600398-95-4 C8H2D8N2
6-(methyl-d3)pyrimidine-2,4(1H,3H)-dione-5-d 6-(methyl-d3)pyrimidine-2,4(1H,3H)-dione-5-d 2600399-75-3 C5H2D4N2O2
5-bromo-2-(cyclopropyl-d5)pyrimidine-4,6-d2 5-bromo-2-(cyclopropyl-d5)pyrimidine-4,6-d2 2600399-27-5 C7BrD7N2
4,6-dibromo-2-(methyl-d3)pyrimidine-5-d 4,6-dibromo-2-(methyl-d3)pyrimidine-5-d 2600400-75-5 C5Br2D4N2
2-chloro-6-(methyl-d3)pyridin-3,5-d2-4-amine 2-chloro-6-(methyl-d3)pyridin-3,5-d2-4-amine 2600399-58-2 C6H2ClD5N2
5-bromo-6-(methyl-d3)pyridin-2-amine 5-bromo-6-(methyl-d3)pyridin-2-amine 2600400-78-8 C6H4BrD3N2
6-bromo-2,8-dimethylimidazo[1,2-b]pyridazine-3,7-d2 6-bromo-2,8-dimethylimidazo[1,2-b]pyridazine-3,7-d2 2645417-00-9 C8H6BrD2N3
6-bromo-2-methyl-8-(methyl-d3)imidazo[1,2-b]pyridazine 6-bromo-2-methyl-8-(methyl-d3)imidazo[1,2-b]pyridazine 2645419-41-4 C8H5BrD3N3
1-(4-bromo-6-fluoropyridin-2-yl-3,5-d2)ethan-1-one-2,2,2-d3 1-(4-bromo-6-fluoropyridin-2-yl-3,5-d2)ethan-1-one-2,2,2-d3 2645416-16-4 C7BrD5FNO
2-aminopyridin-3,5,6-d3-4-ol 2-aminopyridin-3,5,6-d3-4-ol 2645417-13-4 C5H3D3N2O
pyrimidin-4(3H)-one-2,5,6-d3 pyrimidin-4(3H)-one-2,5,6-d3 2645412-69-5 C4HD3N2O
4-bromo-6-(methyl-d3)pyridin-2,5-d2-3-amine 4-bromo-6-(methyl-d3)pyridin-2,5-d2-3-amine 2645413-42-7 C6H2BrD5N2
2,6-bis(methyl-d3)pyridin-4,5-d2-3-amine 2,6-bis(methyl-d3)pyridin-4,5-d2-3-amine 2645412-59-3 C7H2D8N2
2,3-dibromo-6-(methyl-d3)pyridine 2,3-dibromo-6-(methyl-d3)pyridine 2645412-10-6 C6H2Br2D3N
3,5-dibromo-2-(methyl-d3)pyridin-6-d-4-amine 3,5-dibromo-2-(methyl-d3)pyridin-6-d-4-amine 2645416-52-8 C6H2Br2D4N2
3,5-bis(methyl-d3)pyridin-4-amine 3,5-bis(methyl-d3)pyridin-4-amine 2645412-30-0 C7H4D6N2
2-bromo-6-((1-(methyl-d3)azetidin-3-yl-2,2,3,4,4-d5)oxy)pyridine-3,4,5-d3 2-bromo-6-((1-(methyl-d3)azetidin-3-yl-2,2,3,4,4-d5)oxy)pyridine-3,4,5-d3 2645411-87-4 C9BrD11N2O
2-bromo-6-(2-methoxyethoxy)pyridine-3,4,5-d3 2-bromo-6-(2-methoxyethoxy)pyridine-3,4,5-d3 2645418-80-8 C8H7BrD3NO2
2-bromo-4-(2-(methoxy-d3)ethoxy-1,1,2,2-d4)pyridine 2-bromo-4-(2-(methoxy-d3)ethoxy-1,1,2,2-d4)pyridine 2645419-30-1 C8H3BrD7NO2
2-bromo-5-((methoxy-d3)methyl-d2)pyridine 2-bromo-5-((methoxy-d3)methyl-d2)pyridine 2645418-91-1 C7H3BrD5NO
3-bromo-5-(methoxymethyl)pyridine-2,4,6-d3 3-bromo-5-(methoxymethyl)pyridine-2,4,6-d3 2645415-55-8 C7H5BrD3NO
5-bromo-2-((methoxy-d3)methyl-d2)pyrimidine 5-bromo-2-((methoxy-d3)methyl-d2)pyrimidine 2645416-68-6 C6H2BrD5N2O
6-((methoxy-d3)methyl-d2)pyridin-3-amine 6-((methoxy-d3)methyl-d2)pyridin-3-amine 2645420-03-5 C7H5D5N2O
3-fluoro-4-(methyl-d3)pyridin-5,6-d2-2-amine 3-fluoro-4-(methyl-d3)pyridin-5,6-d2-2-amine 2645412-28-6 C6H2D5FN2
4-(methyl-d3)pyridin-2,5,6-d3-3-amine 4-(methyl-d3)pyridin-2,5,6-d3-3-amine 2645418-90-0 C6H2D6N2
2-isopropyl-4-methylpyridin-5,6-d2-3-amine 2-isopropyl-4-methylpyridin-5,6-d2-3-amine 2645416-66-4 C9H12D2N2
4-bromo-2-methylpyridine-3,5,6-d3 4-bromo-2-methylpyridine-3,5,6-d3 2645412-36-6 C6H3BrD3N
5-bromo-2-methylpyridine-3,4,6-d3 5-bromo-2-methylpyridine-3,4,6-d3 2645419-50-5 C6H3BrD3N
6-methylpyridin-2,4,5-d3-3-ol 6-methylpyridin-2,4,5-d3-3-ol 2645411-94-3 C6H4D3NO
4-methylpyridin-2,5,6-d3-3-ol 4-methylpyridin-2,5,6-d3-3-ol 2645415-83-2 C6H4D3NO
5-bromo-N-(methyl-d3)pyridin-2,4,6-d3-3-amine 5-bromo-N-(methyl-d3)pyridin-2,4,6-d3-3-amine 2645412-14-0 C6HBrD6N2
2-bromo-4-fluoro-6-methylpyridine-3,5-d2 2-bromo-4-fluoro-6-methylpyridine-3,5-d2 2645415-97-8 C6H3BrD2FN
1H-pyrrolo[2,3-c]pyridine-2,5,7-d3 1H-pyrrolo[2,3-c]pyridine-2,5,7-d3 2697155-23-8 C7H3D3N2
1H-pyrrolo[2,3-c]pyridine-2,4,5,7-d4 1H-pyrrolo[2,3-c]pyridine-2,4,5,7-d4 2697155-90-9 C7H2D4N2
tert-butyl 4-(6-bromopyridin-2-yl-3,4,5-d3)piperidine-1-carboxylate tert-butyl 4-(6-bromopyridin-2-yl-3,4,5-d3)piperidine-1-carboxylate 2697155-30-7 C15H18BrD3N2O2
tert-butyl 4-(5-bromopyrimidin-2-yl)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 tert-butyl 4-(5-bromopyrimidin-2-yl)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 2697156-80-0 C14H11BrD9N3O2
3-bromo-5-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 3-bromo-5-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 2697156-31-1 C10H7BrD5NO
2-bromo-5-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine-3,4,6-d3 2-bromo-5-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine-3,4,6-d3 2697155-79-4 C10H4BrD8NO
5-bromo-2-(tetrahydro-2H-pyran-4-yl)pyrimidine-4,6-d2 5-bromo-2-(tetrahydro-2H-pyran-4-yl)pyrimidine-4,6-d2 2697156-35-5 C9H9BrD2N2O
4-bromo-2,6-bis(methyl-d3)pyrimidine-5-d 4-bromo-2,6-bis(methyl-d3)pyrimidine-5-d 2697156-88-8 C6BrD7N2
3-bromo-4-methoxypyridine-2,5,6-d3 3-bromo-4-methoxypyridine-2,5,6-d3 2697156-50-4 C6H3BrD3NO
6-(tert-butyl)pyridin-2,4,5-d3-3-amine 6-(tert-butyl)pyridin-2,4,5-d3-3-amine 2697156-54-8 C9H11D3N2
6-(ethyl-d5)pyridin-3,4,5-d3-2-amine 6-(ethyl-d5)pyridin-3,4,5-d3-2-amine 2697155-83-0 C7H2D8N2
2-(ethyl-d5)pyridin-3,5,6-d3-4-amine 2-(ethyl-d5)pyridin-3,5,6-d3-4-amine 2697155-84-1 C7H2D8N2
methyl 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylate-2,2,3,3,5,6,6-d7 methyl 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylate-2,2,3,3,5,6,6-d7 2697156-53-7 C8H6D7NO2
2,4-dibromo-5-(methoxy-d3)pyridine 2,4-dibromo-5-(methoxy-d3)pyridine 2697156-17-3 C6H2Br2D3NO
6-(difluoromethyl)pyridin-2,4,5-d3-3-amine 6-(difluoromethyl)pyridin-2,4,5-d3-3-amine 2697162-73-3 C6H3D3F2N2
5-bromo-2,2'-bipyridine-3,3',4,4',5',6,6'-d7 5-bromo-2,2'-bipyridine-3,3',4,4',5',6,6'-d7 2711075-28-2 C10BrD7N2
2,2'-bipyridin]-d7-5-amine 2,2'-bipyridin]-d7-5-amine 2711075-33-9 C10H2D7N3
5-bromo-4-chloro-2-(difluoromethyl)pyridine-3,6-d2 5-bromo-4-chloro-2-(difluoromethyl)pyridine-3,6-d2 2710298-42-1 C6HBrClD2F2N
2-bromo-3-(trifluoromethyl)pyridine-4,5,6-d3 2-bromo-3-(trifluoromethyl)pyridine-4,5,6-d3 2768654-96-0 C6BrD3F3N
2-bromo-4-(difluoromethyl)pyridine-3,5,6-d3 2-bromo-4-(difluoromethyl)pyridine-3,5,6-d3 2768654-32-4 C6HBrD3F2N
tert-butyl 4-(6-bromopyridin-2-yl-3,4,5-d3)piperazine-1-carboxylate tert-butyl 4-(6-bromopyridin-2-yl-3,4,5-d3)piperazine-1-carboxylate 2768654-64-2 C14H17BrD3N3O2
tert-butyl 3-(2-bromopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate tert-butyl 3-(2-bromopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate 2768654-38-0 C15H18BrD3N2O2
tert-butyl 3-(2-aminopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate tert-butyl 3-(2-aminopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate 2768655-40-7 C15H20D3N3O2
tert-butyl 3-(5-aminopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-aminopyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768655-47-4 C15H11D12N3O2
tert-butyl 3-(5-aminopyridin-2-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-aminopyridin-2-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768657-78-7 C15H14D9N3O2
2-(trifluoromethyl)pyridin-4,5,6-d3-3-amine 2-(trifluoromethyl)pyridin-4,5,6-d3-3-amine 2768657-81-2 C6H2D3F3N2
5-bromo-6-(ethyl-d5)pyridin-3,4-d2-2-amine 5-bromo-6-(ethyl-d5)pyridin-3,4-d2-2-amine 2768655-84-9 C7H2BrD7N2
3-bromo-4-methyl-2-(methyl-d3)pyridine 3-bromo-4-methyl-2-(methyl-d3)pyridine 2396515-75-4 C7H5BrD3N
4-bromo-2-chloro-6-(methoxy-d3)pyridine 4-bromo-2-chloro-6-(methoxy-d3)pyridine 2806718-50-1 C6H2BrClD3NO
2-(2-hydroxypropan-2-yl)pyrimidin-4,6-d2-5-ol 2-(2-hydroxypropan-2-yl)pyrimidin-4,6-d2-5-ol 2806720-94-3 C7H8D2N2O2
2-chloro-5-ethylpyridin-3,6-d2-4-amine 2-chloro-5-ethylpyridin-3,6-d2-4-amine 2806729-47-3 C7H7ClD2N2
2-chloro-3-(methyl-d3)pyridin-5,6-d2-4-amine 2-chloro-3-(methyl-d3)pyridin-5,6-d2-4-amine 2806729-01-9 C6H2ClD5N2
4-bromo-3-methylpyridine-2,5,6-d3 4-bromo-3-methylpyridine-2,5,6-d3 2806729-35-9 C6H3BrD3N
5-bromo-1-(difluoromethyl)pyridin-2(1H)-one-3,4,6-d3 5-bromo-1-(difluoromethyl)pyridin-2(1H)-one-3,4,6-d3 2806720-56-7 C6HBrD3F2NO
1,3-bis(methyl-d3)pyridin-2(1H)-one-4,5,6-d3 1,3-bis(methyl-d3)pyridin-2(1H)-one-4,5,6-d3 2826917-54-6 C7D9NO
2,5-bis(methyl-d3)-6-(trifluoromethyl)pyridin-4-d-3-amine 2,5-bis(methyl-d3)-6-(trifluoromethyl)pyridin-4-d-3-amine 2826916-68-9 C8H2D7F3N2
1,2,4]triazolo[1,5-a]pyridin-d4-7-amine 1,2,4]triazolo[1,5-a]pyridin-d4-7-amine 2826917-17-1 C6H2D4N4
5-methoxy-6-(methyl-d3)pyridin-2,4-d2-3-amine 5-methoxy-6-(methyl-d3)pyridin-2,4-d2-3-amine 2826916-37-2 C7H5D5N2O
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