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【结 构 式】

【分子编号】35069

【品名】(2S)-1-amino-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol

【CA登记号】

【 分 子 式 】C16H27N3O2

【 分 子 量 】293.4094

【元素组成】C 65.5% H 9.28% N 14.32% O 10.91%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(IV)

Alkylation of 1-(2-isopropoxyphenyl)piperazine (I) with 1-azido-3-(p-toluenesulfonyloxy)-2-propanol (II) in hot NMP gave (III). Subsequent hydrogenation of the azido group of (III) over Pd/C provided the intermediate amine (IV).

1 Prouty, C.; Wang, J.; Kuo, G.-H.; Pulito, V.; Murray, W.V.; Cheung, P.; Jolliffe, L.; Varga, S.; Evangelisto, M.; Design, synthesis, and structure-activity relationships of phthalimide-phenylpiperazines: A novel series of potent and selective alpha1a-adrenergic receptor antagonists. J Med Chem 2000, 43, 11, 2183.
2 Murray, W.V.; Kuo, G.-H.; Prouty, C.P. (Ortho-McNeil Pharmaceutical, Inc.); Phthalimido arylpiperazines as alpha 1a receptor antagonists useful in the treatment of benign prostatic hyperplasia. US 6063785; WO 9942445 .
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) 35066 isopropyl 2-(1-piperazinyl)phenyl ether; 1-(2-isopropoxyphenyl)piperazine C13H20N2O 详情 详情
(II) 35067 (2S)-3-azido-2-hydroxypropyl 4-methylbenzenesulfonate C10H13N3O4S 详情 详情
(III) 35068 (2R)-1-azido-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol C16H25N5O2 详情 详情
(IV) 35069 (2S)-1-amino-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol C16H27N3O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

(S)-Epichlorhydrin (V) was treated with benzylamine to afford aminoalcohol (VI). After protection of the amino group of (VI) as the tert-butyl carbamate (VII) with Boc2O, displacement of the chlorine of (VII) with arylpiperazine (I) furnished (VIII). Deprotection of the N-Boc group of (VIII) by means of trifluoroacetic acid gave (IX). Then, the N-benzyl group of (IX) was removed by transfer hydrogenolysis employing ammonium formate and Pd/C to provide the intermediate amine (IV).

1 Prouty, C.; Wang, J.; Kuo, G.-H.; Pulito, V.; Murray, W.V.; Cheung, P.; Jolliffe, L.; Varga, S.; Evangelisto, M.; Design, synthesis, and structure-activity relationships of phthalimide-phenylpiperazines: A novel series of potent and selective alpha1a-adrenergic receptor antagonists. J Med Chem 2000, 43, 11, 2183.
2 Murray, W.V.; Kuo, G.-H.; Prouty, C.P. (Ortho-McNeil Pharmaceutical, Inc.); Phthalimido arylpiperazines as alpha 1a receptor antagonists useful in the treatment of benign prostatic hyperplasia. US 6063785; WO 9942445 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(I) 35066 isopropyl 2-(1-piperazinyl)phenyl ether; 1-(2-isopropoxyphenyl)piperazine C13H20N2O 详情 详情
(IV) 35069 (2S)-1-amino-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol C16H27N3O2 详情 详情
(V) 13917 (S)-Epichlorohydrin; (2S)-2-(Chloromethyl)oxirane;(S)-(+)-epichlorohydrin 67843-74-7 C3H5ClO 详情 详情
(VI) 35070 (2S)-1-(benzylamino)-3-chloro-2-propanol C10H14ClNO 详情 详情
(VII) 35071 tert-butyl benzyl[(2S)-3-chloro-2-hydroxypropyl]carbamate C15H22ClNO3 详情 详情
(VIII) 35072 tert-butyl benzyl[(2R)-2-hydroxy-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]propyl]carbamate C28H41N3O4 详情 详情
(IX) 35073 (2S)-1-(benzylamino)-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol C23H33N3O2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(IV)

Condensation of 1,2,4-benzenetricarboxylic anhydride (X) with N,N-dimethyl-p-phenylenediamine (XI) in boiling AcOH produced phthalimide (XII). The title amide was then obtained by coupling of acid (XII) with amine (IV) in the presence of HATU, or EDC, HOBt and DMAP in dichloromethane.

1 Prouty, C.; Wang, J.; Kuo, G.-H.; Pulito, V.; Murray, W.V.; Cheung, P.; Jolliffe, L.; Varga, S.; Evangelisto, M.; Design, synthesis, and structure-activity relationships of phthalimide-phenylpiperazines: A novel series of potent and selective alpha1a-adrenergic receptor antagonists. J Med Chem 2000, 43, 11, 2183.
2 Murray, W.V.; Kuo, G.-H.; Prouty, C.P. (Ortho-McNeil Pharmaceutical, Inc.); Phthalimido arylpiperazines as alpha 1a receptor antagonists useful in the treatment of benign prostatic hyperplasia. US 6063785; WO 9942445 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 35069 (2S)-1-amino-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol C16H27N3O2 详情 详情
(X) 35074 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylic acid 552-30-7 C9H4O5 详情 详情
(XI) 35075 N-(4-aminophenyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,4-benzenediamine 6219-73-4 C8H12N2 详情 详情
(XII) 35076 2-[4-(dimethylamino)phenyl]-1,3-dioxo-5-isoindolinecarboxylic acid C17H14N2O4 详情 详情
Extended Information