N-(3-chlorophenyl)-2-[(2-hydroxyethyl)amino]acetamide -Drug Synthesis Database

【结构式】

【分子编号】47291

【品名】N-(3-chlorophenyl)-2-[(2-hydroxyethyl)amino]acetamide

【CA登记号】

【分子式】C₁₀H₁₃ClN₂O₂

【分子量】228.6782

【元素组成】C 52.52% H 5.73% Cl 15.5% N 12.25% O 13.99%

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：(XI)

In an alternative procedure, 3-chloroaniline (I) was acylated with chloroacetyl chloride (V) to produce chloroacetamide (IX). Displacement of the chloride group of (IX) with ethanolamine (X) gave rise to the amide alcohol (XI), which was then cyclized to the piperazinone (VIII) under Mitsunobu conditions.

参考文献中间体

合成目标

【1】 Cowen, J.A.; Askin, D.; McWilliams, J.C.; Maligres, P.E.; McCauley, J.A. (Merck & Co., Inc.); Process for making farnesyl-protein transferase inhibitors. WO 0001691 .

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)	25239	3-chloroaniline; 3-chlorophenylamine	108-42-9	C₆H₆ClN	详情	详情
(V)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(VIII)	47289	1-(3-chlorophenyl)-2-piperazinone		C₁₀H₁₁ClN₂O	详情	详情
(IX)	47290	2-chloro-N-(3-chlorophenyl)acetamide		C₈H₇Cl₂NO	详情	详情
(X)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(XI)	47291	N-(3-chlorophenyl)-2-[(2-hydroxyethyl)amino]acetamide		C₁₀H₁₃ClN₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

3-Chloroaniline (I) was acylated with chloroacetyl chloride (II) in isopropyl acetate. The resulting chloroacetanilide (III) was condensed with ethanolamine (IV) to yield the (hydroxyethyl)glycinamide (V). Cyclization of (V) to produce the piperazinone (VI) was then effected by treatment with di-tert-butyl azodicarboxylate and tributylphosphine.

参考文献中间体

合成目标

【1】 Williams, T.M. (Merck & Co., Inc.); Biaryl inhibitors of prenyl-protein transferase. WO 0075135 .

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)	25239	3-chloroaniline; 3-chlorophenylamine	108-42-9	C₆H₆ClN	详情	详情
(II)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(III)	47290	2-chloro-N-(3-chlorophenyl)acetamide		C₈H₇Cl₂NO	详情	详情
(IV)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(V)	47291	N-(3-chlorophenyl)-2-[(2-hydroxyethyl)amino]acetamide		C₁₀H₁₃ClN₂O₂	详情	详情
(VI)	47289	1-(3-chlorophenyl)-2-piperazinone		C₁₀H₁₁ClN₂O	详情	详情

Extended Information