N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide -Drug Synthesis Database

【结构式】

【分子编号】24645

【品名】N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide

【CA登记号】

【分子式】C₉H₇BrN₄S

【分子量】283.15154

【元素组成】C 38.18% H 2.49% Br 28.22% N 19.79% S 11.32%

与该中间体有关的原料药合成路线共 7 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6 合成路线7

合成路线1

该中间体在本合成路线中的序号：(III)

Condensation of 2-amino-5-bromopyridine (I) with 1,1-thiocarbonyl diimidazole (II) furnished the thiocarbonyl derivative (III). Further reaction of (III) with 1-(2-aminoethyl)piperidine (IV) gave the target thiourea.

参考文献中间体

合成目标

【1】 Mao, C.; Vig, R.; Venkatachalam, T.K.; Sudbeck, E.A.; Uckun, F.M.; Structure-based design of N-[2-(1-piperidinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 1998, 8, 16, 2213.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(II)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(III)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(IV)	24646	2-(1-piperidinyl)-1-ethanamine	27578-60-5	C₇H₁₆N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Mao, C.; Vig, R.; Venkatachalam, T.K.; Sudbeck, E.A.; Uckun, F.M.; Structure-based design of N-[2-(1-piperidinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 1998, 8, 16, 2213.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(II)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(III)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(IV)	24647	2-(1-piperazinyl)-1-ethanamine	140-31-8	C₆H₁₅N₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

The reaction of 5-bromopyridin-2-amine (I) with thiocarbonyldiimidazole (II) in acetonitrile gives the thioamide (III), which is finally condensed with 2-(2,5-dimethoxyphenyl)ethylamine (IV) in DMF at 100 C.

参考文献中间体

合成目标

【1】 Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel-Ahlgren, L.; Sudbeck, E.A.; Uckun, F.M.; Rational design and synthesis of phenethyl-5-bromopyridyl thiourea derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase. Bioorg Med Chem 1998, 6, 10, 1789.
【2】 Uckun, F.M. (Parker Hughes Institute); NNI for treatment of multi-drug resistant HIV. WO 0056736 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(II)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(III)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(IV)	36889	2,5-dimethoxyphenethylamine; 2-(2,5-dimethoxyphenyl)-1-ethanamine	3600-86-0	C₁₀H₁₅NO₂	详情	详情

合成路线4

该中间体在本合成路线中的序号：(IV)

Alternatively, 2-amino-5-bromopyridine (I) was reacted with 1,1'-thiocarbonyldiimidazole (III) in acetonitrile yielding thioimidazolide (IV), which was then condensed with 2-(1-cyclohexenyl)ethylamine (V) in hot DMF.

参考文献中间体

合成目标

【1】 Maher, D.; Mao, C.; Pendergrass, S.; Venkatachalam, T.K.; Zhu, D.; Tuel-Ahlgren, L.; Uckun, F.M.; N-[2-(1-Cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1. Bioorg Med Chem Lett 1999, 9, 18, 2721.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(III)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(IV)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(V)	36902	2-(1-cyclohexen-1-yl)ethylamine; 2-(1-cyclohexen-1-yl)-1-ethanamine; 2-(1-Cyclohexenyl)ethylamine	3399-73-3	C₈H₁₅N	详情	详情

合成路线5

该中间体在本合成路线中的序号：(III)

Reaction of 2-amino-5-bromopyridine (I) with thiocarbonyl diimidazole (II) provided the thioimidazolide (III). This was then coupled with 2-(2-thienyl)ethyl amine (IV) to furnish the target thiourea.

参考文献中间体

合成目标

【1】 Maher, D.; Mao, C.; Tuel-Ahlgren, L.; Uckun, F.M.; Zhu, D.; Pendergrass, S.; Venkatachalam, T.K.; N'-[2-(2-Thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1. Bioorg Med Chem Lett 1999, 9, 24, 3411.
【2】 Ventatachalam, T.K.; Uckun, F.M. (Parker Hughes Institute); Thiophene-ethyl thiourea cpds. and use. US 6124324; WO 0078755 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(II)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(III)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(IV)	35253	2-(2-thienyl)ethylamine; 2-(2-thienyl)-1-ethanamine; 2-Thiophene ethylamine	30433-91-1	C₆H₉NS	详情	详情

合成路线6

该中间体在本合成路线中的序号：(III)

Reaction of 2-amino-5-bromopyridine (I) with thiocarbonyldiimidazole (II) afforded the thioimidazolide (III). This was then condensed with 4-methylphenetylamine (IV) in hot DMF to produce the required thiourea.

参考文献中间体

合成目标

【2】 Ventalachalam, T.K.; Uckum, F.M. (Parker Hughes Institute); Phenethyl-thiourea cpds. and use. US 6207688 .
【1】 Uckun, F.M.; Zhu, D.; Pendergrass, S.; Mao, C.; Tuel-Ahlgren, L.; Venkatachalam, T.K.; Maher, D.; N-[2-(4-Methylphenyl)ethyl]-N'-[2-(5-bromopyridyl)]thiourea as a potent inhibitor of NNRTI-resistant and multidrug-resistant human immunodeficiency virus type 1. Antivir Chem Chemother 2000, 11, 2, 135.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(II)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(III)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(IV)	46291	4-methylphenethylamine; 2-(4-methylphenyl)-1-ethanamine		C₉H₁₃N	详情	详情

合成路线7

该中间体在本合成路线中的序号：(III)

Condensation of 2-amino-5-bromopyridine (I) with thiocarbonyl diimidazole (II) gave rise to thioimidazolide (III), which was then condensed with (R)-1-phenylethylamine (IV) to yield the title thiourea.

参考文献中间体

合成目标

【1】 Mao, C.; Venkatachalam, T.K.; Uckun, F.M.; Sudbeck, E.A.; Stereochemistry of halopyridyl and thiazolyl thiourea compounds is a major determinant of their potency as nonnucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2000, 10, 18, 2071.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12123	5-Bromo-2-pyridinylamine; 5-Bromo-2-pyridinamine; 2-Amino-5-bromopyridine	1072-97-5	C₅H₅BrN₂	详情	详情
(II)	11990	Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldiimidazole	6160-65-2	C₇H₆N₄S	详情	详情
(III)	24645	N-(5-bromo-2-pyridinyl)-1H-imidazole-1-carbothioamide		C₉H₇BrN₄S	详情	详情
(IV)	10039	(1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine	3886-69-9	C₈H₁₁N	详情	详情

Extended Information