(3-amino-1H-pyrazol-4-yl)(2-thienyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】59946

【品名】(3-amino-1H-pyrazol-4-yl)(2-thienyl)methanone

【CA登记号】

【分子式】C₈H₇N₃OS

【分子量】193.2292

【元素组成】C 49.73% H 3.65% N 21.75% O 8.28% S 16.59%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

Condensation of 2-acetylthiophene (I) with dimethylformamide dimethylacetal produced enaminone (II), which was subsequently cyclized to the isoxazole (III) upon treatment with hydroxylamine. Further condensation of (III) with dimethylformamide dimethylacetal, with concomitant isoxazole ring opening, gave rise to the enamino nitrile (IV). This was then cyclized with aminoguanidine nitrate (V) under basic conditions to furnish the intermediate aminopyrazole (VI).

参考文献中间体

合成目标

【2】 Tomcufcik, A.S.; Dusza, J.P.; Albright, J.D.; Beer, B. (Wyeth); N-Methyl-N-(-[3-[-2-thienylcarbonyl]-pyrazol-[1,5-alpha]-pyrimidin-7-yl]phenyl)acetamide and compsns. and methods related thereto. US 6399621 .
【1】 Sorbera, L.A.; Castaner, J.; Martin, L.; Indiplon. Drugs Fut 2003, 28, 8, 739.

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)	24490	1-(2-Thienyl)-1-ethanone; 2-Acetylthiophene	88-15-3	C₆H₆OS	详情	详情
(II)	59943	(E)-3-(dimethylamino)-1-(2-thienyl)-2-propen-1-one		C₉H₁₁NOS	详情	详情
(III)	59944	5-(2-thienyl)isoxazole		C₇H₅NOS	详情	详情
(IV)	59945	(E)-3-(dimethylamino)-2-(2-thienylcarbonyl)-2-propenenitrile		C₁₀H₁₀N₂OS	详情	详情
(V)	10015	1-Hydrazinecarboximidamide; Hydrazinecarboximidamide	79-17-4	CH₆N₄	详情	详情
(VI)	59946	(3-amino-1H-pyrazol-4-yl)(2-thienyl)methanone		C₈H₇N₃OS	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

3-(Acetamido)acetophenone (VII) was converted to enaminone (VIII) upon condensation with dimethylformamide dimethylacetal. The amide N of (VIII) was then alkylated by means of iodomethane and NaH or, alternatively, under phase-transfer conditions to give (IX). Finally, condensation between enaminone (IX) and aminopyrazole (VI) in refluxing AcOH provided the target pyrazolopyrimidine.

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】 Dusza, J.P.; Tomcufcik, A.S.; Albright, J.D. (Wyeth); Aryl and heteroaryl 7-(aryl and heteroaryl)-pyrazolo[1,5-a]pyrimidin-3-ylmethanones. DE 3422844; EP 0129847; JP 1985019788 .
【3】 Tomcufcik, A.S.; Dusza, J.P.; Albright, J.D.; Beer, B. (Wyeth); N-Methyl-N-(-[3-[-2-thienylcarbonyl]-pyrazol-[1,5-alpha]-pyrimidin-7-yl]phenyl)acetamide and compsns. and methods related thereto. US 6399621 .
【4】 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
(VI)	59946	(3-amino-1H-pyrazol-4-yl)(2-thienyl)methanone		C₈H₇N₃OS	详情	详情
(VII)	11983	3'-Acetamidoacetophane; m-Acetamidoacetophenone; N-(3-Acetylphenyl)acetamide	7463-31-2	C₁₀H₁₁NO₂	详情	详情
(VIII)	11985	N-[3-[(E)-3-(Dimethylamino)-2-propenoyl]phenyl]acetamide		C₁₃H₁₆N₂O₂	详情	详情
(IX)	59947	N-{3-[(E)-3-(dimethylamino)-2-propenoyl]phenyl}-N-methylacetamide		C₁₄H₁₈N₂O₂	详情	详情

Extended Information