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【结 构 式】

【分子编号】62021

【品名】2-(4-{benzyl[(2R)-3,4-dihydro-2H-chromen-2-ylmethyl]amino}butyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione

【CA登记号】

【 分 子 式 】C28H30N2O4S

【 分 子 量 】490.62328

【元素组成】C 68.55% H 6.16% N 5.71% O 13.04% S 6.54%

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:(IX)

The reaction of labeled 2-hydroxyacetophenone (I) with dimethyl oxalate and NaOMe gives 4-oxo-4H-1-benzopyran-2-carboxylic acid methyl ester (II), which is hydrogenated with H2 over Pd/C to yield 3,4-dihydro-2H-1-benzopyran-2(R)-carboxylic acid methyl ester (III). The optical resolution of (III) by chiral chromatography affords the labeled (R)-enantiomer (IV), which is condensed with benzylamine (V) to provide the corresponding amide (VI). The reduction of (VI) by means of NaAlH2(OC2H4OMe)2 gives the labeled chiral amine (VII), which is condensed with the butyl bromide derivative (VIII) to yield the tertiary amine (IX). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C to afford the target labeled Repinotan.

1 Seidel, D.; et al.; Synthesis of [14C]-labelled repinotan hydrochloride and its major metabolite M-6. J Label Compd Radiopharm 2002, 45, 13, 1115.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
37412 methyl 2-methoxy-2-oxoacetate;dimethyl oxalate;Methyl oxalate 553-90-2 C4H6O4 详情 详情
(I) 29654 2-hydroxyacetophenone; 1-(2-hydroxyphenyl)-1-ethanone 118-93-4 C8H8O2 详情 详情
(II) 62016 methyl 4-oxo-4H-chromene-2-carboxylate C11H8O4 详情 详情
(III) 62017 methyl 2-chromanecarboxylate C11H12O3 详情 详情
(IV) 62018 methyl (2R)-3,4-dihydro-2H-chromene-2-carboxylate C11H12O3 详情 详情
(V) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(VI) 62019 (2R)-N-benzyl-3,4-dihydro-2H-chromene-2-carboxamide C17H17NO2 详情 详情
(VII) 62020 N-benzyl-N-[(2R)-3,4-dihydro-2H-chromen-2-ylmethyl]amine; N-benzyl[(2R)-3,4-dihydro-2H-chromen-2-yl]methanamine C17H19NO 详情 详情
(VIII) 17043 2-(4-bromobutyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione C11H12BrNO3S 详情 详情
(IX) 62021 2-(4-{benzyl[(2R)-3,4-dihydro-2H-chromen-2-ylmethyl]amino}butyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione C28H30N2O4S 详情 详情
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