ethyl 2-{[(tert-butylamino)carbonyl]amino}-1,3-benzothiazole-6-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】65036

【品名】ethyl 2-{[(tert-butylamino)carbonyl]amino}-1,3-benzothiazole-6-carboxylate

【CA登记号】

【分子式】C₁₅H₁₉N₃O₃S

【分子量】321.40028

【元素组成】C 56.06% H 5.96% N 13.07% O 14.93% S 9.98%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

Reaction of ethyl 4-aminobenzoate (I) with sodium thiocyanate and bromine in cold AcOH gives rise to the amino benzothiazole (II). Subsequent treatment of (II) with phenyl chloroformate affords the phenyl carbamate (III), which is further reacted with tert-butylamine to furnish urea (IV). After alkaline hydrolysis of the ethyl ester (IV), the resultant carboxylic acid (V) is converted to the azabenzotriazolyl active ester (VI) upon treatment with HATU in DMF. Active ester (VI) is finally coupled with 2-chloro-6-methylaniline (VII) in the presence of sodium bis(trimethylsilyl)amide to yield the target amide.

参考文献中间体

合成目标

【1】 Das, J.; Barrish, J.C.; Wityak, J. (Bristol-Myers Squibb Co.); Benzothiazole protein tyrosine kinase inhibitors. EP 1037632; JP 2001522800; WO 9924035 .

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)	16498	Benzocaine; ethyl 4-aminobenzoate	94-09-7	C₉H₁₁NO₂	详情	详情
(II)	65034	ethyl 2-amino-1,3-benzothiazole-6-carboxylate		C₁₀H₁₀N₂O₂S	详情	详情
(III)	65035	ethyl 2-[(phenoxycarbonyl)amino]-1,3-benzothiazole-6-carboxylate		C₁₇H₁₄N₂O₄S	详情	详情
(IV)	65036	ethyl 2-{[(tert-butylamino)carbonyl]amino}-1,3-benzothiazole-6-carboxylate		C₁₅H₁₉N₃O₃S	详情	详情
(V)	65037	2-{[(tert-butylamino)carbonyl]amino}-1,3-benzothiazole-6-carboxylic acid		C₁₃H₁₅N₃O₃S	详情	详情
(VI)	65038	N-(tert-butyl)-N'-{6-[(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)carbonyl]-1,3-benzothiazol-2-yl}urea		C₁₈H₁₇N₇O₃S	详情	详情
(VII)	29789	2-chloro-6-methylphenylamine; 2-chloro-6-methylaniline	87-63-8	C₇H₈ClN	详情	详情

Extended Information