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【结 构 式】

【分子编号】58455

【品名】8-(chloromethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine

【CA登记号】

【 分 子 式 】C11H8ClN3S

【 分 子 量 】249.72344

【元素组成】C 52.91% H 3.23% Cl 14.2% N 16.83% S 12.84%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Displacement of the chloride group of 4-chloro-3-nitrobenzoic acid (I) with sodium disulfide, followed by reduction of the disulfide and nitro groups with Sn/HCl yields 3-amino-4-mercaptobenzoic acid (II), which is further esterified to (III) with methanolic HCl. Condensation of (III) with 2,3-dichloropyrazine (IV) produces the pyrazinobenzothiazine compound (V). The ester group of (V) is then reduced to alcohol (VI) employing LiAlH4. Subsequent treatment of alcohol (VI) with methanesulfonyl chloride and pyridine leads to the benzyl chloride (VII).

1 Kaneko, T.; et al.; Inhibitors of adhesion molecules expression: The synthesis and pharmacological properties of 10H-pyrazino[2,3-b][1,4]benzothiazine derivatives. Chem Pharm Bull 2002, 50, 7, 922.
2 Kaneko, T.; Clark, R.; Ohi, N.; Ozaki, F.; Kawahara, T.; Kamada, A.; Okano, K.; Yokohama, H.; Muramoto, K.; Arai, T.; Ohkuro, M.; Takenaka, O.; Sonoda, J. (Eisai Co., Ltd.); Benzopiperidine derivs.. EP 0934941; WO 9806720 .
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) 14485 3-nitro-4-chlorobenzoic acid; 4-chloro-3-nitrobenzoic acid 96-99-1 C7H4ClNO4 详情 详情
(II) 58451 3-amino-4-sulfanylbenzoic acid C7H7NO2S 详情 详情
(III) 58452 methyl 3-amino-4-sulfanylbenzoate C8H9NO2S 详情 详情
(IV) 32326 2,3-dichloropyrazine 4858-85-9 C4H2Cl2N2 详情 详情
(V) 58453 methyl 10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxylate C12H9N3O2S 详情 详情
(VI) 58454 10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethanol C11H9N3OS 详情 详情
(VII) 58455 8-(chloromethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine C11H8ClN3S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

4-Amino-1-benzylpiperidine (VIII) is condensed with dimethylsulfamoyl chloride to give the sulfamide (IX). Subsequent benzyl group hydrogenolysis in (IX) over Pd/C provides the piperidine (X). Finally, alkylation of piperidine (X) with chloride (VII) yields the title compound.

1 Kaneko, T.; et al.; Inhibitors of adhesion molecules expression: The synthesis and pharmacological properties of 10H-pyrazino[2,3-b][1,4]benzothiazine derivatives. Chem Pharm Bull 2002, 50, 7, 922.
2 Kaneko, T.; Clark, R.; Ohi, N.; Ozaki, F.; Kawahara, T.; Kamada, A.; Okano, K.; Yokohama, H.; Muramoto, K.; Arai, T.; Ohkuro, M.; Takenaka, O.; Sonoda, J. (Eisai Co., Ltd.); Benzopiperidine derivs.. EP 0934941; WO 9806720 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 58455 8-(chloromethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine C11H8ClN3S 详情 详情
(VIII) 34808 1-Benzyl-4-piperidinylamine; 1-Benzyl-4-piperidinamine; 4-Amino-1-benzylpiperidine 50541-93-0 C12H18N2 详情 详情
(IX) 58456 N'-(1-benzyl-4-piperidinyl)-N,N-dimethylsulfamide C14H23N3O2S 详情 详情
(X) 58457 N,N-dimethyl-N'-(4-piperidinyl)sulfamide C7H17N3O2S 详情 详情
Extended Information