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【结 构 式】

【分子编号】64055

【品名】1,1-dimethylethyl 2-(4-{3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl}-1,4-diazepan-1-yl)-2-oxo-1-(1,3-thiazol-4-ylmethyl)ethylcarbamate

【CA登记号】

【 分 子 式 】C32H39N5O4S

【 分 子 量 】589.75896

【元素组成】C 65.17% H 6.67% N 11.87% O 10.85% S 5.44%

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:(VIII)

Alkylation of 4-cyano-4'-hydroxybiphenyl (I) with 1-bromo-3-chloropropane (II) yields the chloropropyl ether (III). This is then condensed with the mono-protected homopiperazine (IV) to furnish (V). Removal of the N-Boc group of (V) to afford amine (VI) is then accomplished by treatment with trifluoroacetic acid in CH2Cl2. Amine (VI) is subsequently coupled with N-Boc-D-thiazolylalanine (VII) in the presence of EDC/DMAP producing amide (VIII). (1,2)

1 Curtis, M.P.; Dwight, W.; Fox, G.B.; Esbenshade, T.A.; Pan, J-B.; Bennani, Y.L.; Hancock, A.A.; Faghih, R.; A-320436: Potent human non-imidazole histamine H3 receptor antagonist. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 240.
2 Black, L.A.; Faghih, R.; Bennani, Y.L.; Liu, H.; Zhang, H.Q.; Dwight, W.J.; Gentles, R.G.; Phelan, K.M.; Vasudevan, A. (Abbott Laboratories Inc.); Cyclic and bicyclic diamino histamine-3 receptor antagonists. WO 0166534 .
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) 48735 4-Cyano-4'-hydroxybiphenyl; 4-Hydroxy-4'-cyanodiphenyl; 4'-Cyano-4-biphenylol; 4'-Hydroxy-4-biphenylcarbonitrile 19812-93-2 C13H9NO 详情 详情
(II) 10358 1-Bromo-3-chloropropane 109-70-6 C3H6BrCl 详情 详情
(III) 57817 4'-(3-chloropropoxy)[1,1'-biphenyl]-4-carbonitrile C16H14ClNO 详情 详情
(IV) 54079 tert-Butyl 1-homopiperazine carboxylate n/a C10H20N2O2 详情 详情
(V) 64053 1,1-dimethylethyl 4-{3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl}-1,4-diazepane-1-carboxylate C26H33N3O3 详情 详情
(VI) 64054 4'-{[3-(1,4-diazepan-1-yl)propyl]oxy}[1,1'-biphenyl]-4-carbonitrile C21H25N3O 详情 详情
(VII) 12882 (2S)-2-[(tert-Butoxycarbonyl)amino]-3-(1,3-thiazol-4-yl)propionic acid C11H16N2O4S 详情 详情
(VIII) 64055 1,1-dimethylethyl 2-(4-{3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl}-1,4-diazepan-1-yl)-2-oxo-1-(1,3-thiazol-4-ylmethyl)ethylcarbamate C32H39N5O4S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VIII)

Acidic cleavage of the N-Boc group of (VIII) furnishes amine (IX). Finally, acylation of (IX) with 2-furoyl chloride (X) leads to the title compound. (1,2)

1 Curtis, M.P.; Dwight, W.; Fox, G.B.; Esbenshade, T.A.; Pan, J-B.; Bennani, Y.L.; Hancock, A.A.; Faghih, R.; A-320436: Potent human non-imidazole histamine H3 receptor antagonist. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 240.
2 Black, L.A.; Faghih, R.; Bennani, Y.L.; Liu, H.; Zhang, H.Q.; Dwight, W.J.; Gentles, R.G.; Phelan, K.M.; Vasudevan, A. (Abbott Laboratories Inc.); Cyclic and bicyclic diamino histamine-3 receptor antagonists. WO 0166534 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 64055 1,1-dimethylethyl 2-(4-{3-[(4'-cyano[1,1'-biphenyl]-4-yl)oxy]propyl}-1,4-diazepan-1-yl)-2-oxo-1-(1,3-thiazol-4-ylmethyl)ethylcarbamate C32H39N5O4S 详情 详情
(IX) 64056 4'-[(3-{4-[2-amino-3-(1,3-thiazol-4-yl)propanoyl]-1,4-diazepan-1-yl}propyl)oxy][1,1'-biphenyl]-4-carbonitrile C27H31N5O2S 详情 详情
(X) 26093 2-Furoyl chloride 527-69-5 C5H3ClO2 详情 详情
Extended Information