1H-pyrazol-5-amine; 1H-pyrazol-5-ylamine -Drug Synthesis Database

【结构式】

【分子编号】56012

【品名】1H-pyrazol-5-amine; 1H-pyrazol-5-ylamine

【CA登记号】916420-28-5

【分子式】C₃H₅N₃

【分子量】83.09292

【元素组成】C 43.36% H 6.07% N 50.57%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

5-Butyl-7-hydroxypyrazolo[1,5-a]pyrimidine (III) was prepared by condensation of 3-aminopyrazole (I) with methyl 3-oxoheptanoate (II) in refluxing toluene. Treatment of (III) with POCl3 in the presence of Et3N furnished the 7-chloro derivative (IV), which was then heated with aqueous ammonia in a sealed tube to afford the amino pyrazolopyrimidine (V). Finally, acylation of amine (V) with 3,4,5-trimethoxybenzoyl chloride (VI) led to the title amide.

参考文献中间体

合成目标

【1】 Shoji, Y.; Yasuda, T.; Inoue, M.; Okamura, T.; Hashimoto, K.; Ohara, M. (Otsuka Pharmaceutical Co., Ltd.); Pyrazolo[1,5-a]pyrimidine deriv.. EP 0714898; JP 1996310951; JP 1996311068; US 5707997; WO 9535298 .

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)	56012	1H-pyrazol-5-amine; 1H-pyrazol-5-ylamine	916420-28-5	C₃H₅N₃	详情	详情
(II)	56013	3-Ketoheptanoic acid methyl ester; 3-Oxokenanthic acid mehyl ester; Methyl 3-oxoheptanoate	39815-78-6	C₈H₁₄O₃	详情	详情
(III)	56014	5-butylpyrazolo[1,5-a]pyrimidin-7-ol		C₁₀H₁₃N₃O	详情	详情
(IV)	56015	5-butyl-7-chloropyrazolo[1,5-a]pyrimidine		C₁₀H₁₂ClN₃	详情	详情
(V)	56016	5-butylpyrazolo[1,5-a]pyrimidin-7-amine; 5-butylpyrazolo[1,5-a]pyrimidin-7-ylamine		C₁₀H₁₄N₄	详情	详情
(VI)	13571	3,4,5Ttrimethoxybenzoyl chloride	4521-61-3	C₁₀H₁₁ClO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XI)

Bromination of 5-aminopyrazole (XI) with Br2 in AcOH gives 4-bromo-5-aminopyrazole (XII), which is cyclized with N-[3-[3-(dimethylamino)-2-propenoyl]phen-yl]-N-methylacetamide (X) in AcOH to yield the 3-bromo-pyrazolo[1,5-a]pyrimidine derivative (XIII). Finally, this compound can be condensed with either 2-thienylcarbonyl chloride (XIV) by means of Zn or Mg or with 2-thienylboronic acid (XV) and CO by means of a Pd(0) catalyst.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castaner, J.; Martin, L.; Indiplon. Drugs Fut 2003, 28, 8, 739.
【2】 Wilcoxen, K.M.; Gross, R.S. (Neurocrine Biosciences Inc.); Synthesis of substd. pyrazolopyrimidines. WO 0110868 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	59947	N-{3-[(E)-3-(dimethylamino)-2-propenoyl]phenyl}-N-methylacetamide		C₁₄H₁₈N₂O₂	详情	详情
(XI)	56012	1H-pyrazol-5-amine; 1H-pyrazol-5-ylamine	916420-28-5	C₃H₅N₃	详情	详情
(XII)	62961	4-bromo-1H-pyrazol-5-ylamine; 4-bromo-1H-pyrazol-5-amine		C₃H₄BrN₃	详情	详情
(XIII)	62962	N-[3-(3-bromopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylacetamide		C₁₅H₁₃BrN₄O	详情	详情
(XIV)	14103	2-Thiophenecarbonyl chloride	5271-67-0	C₅H₃ClOS	详情	详情
(XV)	62963	2-thiophenylboronic acid		C₄H₅BO₂S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XI)

Cyclization of 2-aminopyrazole (XI) with the acetamide (X) in AcOH gives the pyrazolo[1,5-a]pyrimidine derivative (XVI), which is finally acylated with 2-thienylcarbonyl chloride (XIV) by means of AlCl3.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castaner, J.; Martin, L.; Indiplon. Drugs Fut 2003, 28, 8, 739.
【2】 Wilcoxen, K.M.; Gross, R.S. (Neurocrine Biosciences Inc.); Synthesis of substd. pyrazolopyrimidines. WO 0110868 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	59947	N-{3-[(E)-3-(dimethylamino)-2-propenoyl]phenyl}-N-methylacetamide		C₁₄H₁₈N₂O₂	详情	详情
(XI)	56012	1H-pyrazol-5-amine; 1H-pyrazol-5-ylamine	916420-28-5	C₃H₅N₃	详情	详情
(XIV)	14103	2-Thiophenecarbonyl chloride	5271-67-0	C₅H₃ClOS	详情	详情
(XVI)	62964	N-methyl-N-(3-pyrazolo[1,5-a]pyrimidin-7-ylphenyl)acetamide		C₁₅H₁₄N₄O	详情	详情

Extended Information