2-amino-N-(2-chloro-6-methylphenyl)-1,3-benzothiazole-6-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】65043

【品名】2-amino-N-(2-chloro-6-methylphenyl)-1,3-benzothiazole-6-carboxamide

【CA登记号】

【分子式】C₁₅H₁₂ClN₃OS

【分子量】317.7986

【元素组成】C 56.69% H 3.81% Cl 11.16% N 13.22% O 5.03% S 10.09%

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：(VIII)

In an alternative method, ethyl 4-aminobenzoate (I) is treated with NaSCN/Br2 to produce the amino benzothiazole (II), which is further protected as the N-Boc derivative (III). Alkaline hydrolysis of ester (III), followed by chlorination of the resultant acid (IV) with oxalyl chloride gives rise to the acid chloride (V). This is then coupled with 2-chloro-6-methylaniline (VI) yielding amide (VII). The N-Boc protecting group of (VII) is then cleaved employing trifluoroacetic acid to produce amine (VIII), which is subsequently reacted with phenyl chloroformate producing the phenyl carbamate (IX). Finally, displacement of carbamate (IX) with tert-butylamine furnishes the title urea. (1,2)

参考文献中间体

合成目标

【1】 Das, J.; Lin, J.; Moquin, R.V.; Shen, Z.; Spergel, S.H.; Wityak, J.; Doweyko, A.M.; DeFex, H.F.; Fang, Q.; Pang, S.; Pitt, S.; Shen, D.R.; Schieven, G.L.; Barrish, J.C.; Molecular design, synthesis, and structure-activity relationships leading to the potent and selective p56(lck) inhibitor BMS-243117. Bioorg Med Chem Lett 2003, 13, 13, 2145.
【2】 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)	65039	ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-benzothiazole-6-carboxylate		C₁₅H₁₈N₂O₄S	详情	详情
(IV)	65040	2-[(tert-butoxycarbonyl)amino]-1,3-benzothiazole-6-carboxylic acid		C₁₃H₁₄N₂O₄S	详情	详情
(V)	65041	tert-butyl 6-(chlorocarbonyl)-1,3-benzothiazol-2-ylcarbamate		C₁₃H₁₃ClN₂O₃S	详情	详情
(VI)	29787	2-(3-methyl-4-oxo-1,3-thiazolidin-2-ylidene)acetyl chloride		C₆H₆ClNO₂S	详情	详情
(VII)	65042	tert-butyl 6-[(2-chloro-6-methylanilino)carbonyl]-1,3-benzothiazol-2-ylcarbamate		C₂₀H₂₀ClN₃O₃S	详情	详情
(VIII)	65043	2-amino-N-(2-chloro-6-methylphenyl)-1,3-benzothiazole-6-carboxamide		C₁₅H₁₂ClN₃OS	详情	详情
(IX)	65044	phenyl 6-[(2-chloro-6-methylanilino)carbonyl]-1,3-benzothiazol-2-ylcarbamate		C₂₂H₁₆ClN₃O₃S	详情	详情

Extended Information