methyl 3-amino-5-(chloromethyl)benzoate -Drug Synthesis Database

【结构式】

【分子编号】64135

【品名】methyl 3-amino-5-(chloromethyl)benzoate

【CA登记号】

【分子式】C₉H₁₀ClNO₂

【分子量】199.63664

【元素组成】C 54.15% H 5.05% Cl 17.76% N 7.02% O 16.03%

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：(I)

The reductocondensation of 3-amino-5-(chloromethyl)benzoic acid methyl ester (I) with 2-aminothiazol-5-ylisothiocyanate (II) by means of NaBH4 gives the thioether (III), which is condensed with 4-(dimethylamino)benzoyl chloride (IV) by means of pyridine in dichloromethane to yield the amide (V). The hydrolysis of the ester group of (V) with NaOH in methanol affords the corresponding carboxylic acid (VI), which is finally condensed with 1-acetylpiperazine (VII) by means of WSC, HATU and DIEA in THF to provide the target piperazide.

参考文献中间体

合成目标

【1】 Wityak, J.; Das, J.; Liu, C.; Lin, J.; Spergel, S.H.; Moquin, R.V.; Furch, J.A.; Doweiko, A.; Kanner, S.; Lin, T.-A.; Selective Emt inhibitors: Discovery and SAR of 2-amino-[(5-thiomethyl)aryl]thiazoles. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 257.

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)	64135	methyl 3-amino-5-(chloromethyl)benzoate		C₉H₁₀ClNO₂	详情	详情
(II)	64136	2-amino-1,3-thiazole-5-sulfenyl cyanide	23056-10-2	C₄H₃N₃S₂	详情	详情
(III)	64137	methyl 3-amino-5-{[(2-amino-1,3-thiazol-5-yl)sulfanyl]methyl}benzoate		C₁₂H₁₃N₃O₂S₂	详情	详情
(IV)	39988	4-(dimethylamino)benzoyl chloride	4755-50-4	C₉H₁₀ClNO	详情	详情
(V)	64138	methyl 3-amino-5-{[(2-{[4-(dimethylamino)benzoyl]amino}-1,3-thiazol-5-yl)sulfanyl]methyl}benzoate		C₂₁H₂₂N₄O₃S₂	详情	详情
(VI)	64139	3-amino-5-{[(2-{[4-(dimethylamino)benzoyl]amino}-1,3-thiazol-5-yl)sulfanyl]methyl}benzoic acid		C₂₀H₂₀N₄O₃S₂	详情	详情
(VII)	20674	N-Acetyl piperazine; 1-(1-piperazinyl)-1-ethanone	13889-98-0	C₆H₁₂N₂O	详情	详情

Extended Information