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【结 构 式】

【分子编号】41816

【品名】2-methyl-6-[(4-methylphenyl)sulfonyl]-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

【CA登记号】

【 分 子 式 】C19H19N3O2S

【 分 子 量 】353.44488

【元素组成】C 64.57% H 5.42% N 11.89% O 9.05% S 9.07%

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:(XI)

The bromination of 1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one (IX) with Br2 in CHCl3 gives the alpha-bromo ketone (X), which is cyclized with acetamidine hydrochloride (VIII) by means of K2CO3, yielding the expected imidazo-benzazepine (XI). This compound is detosylated with hot H2SO4 to provide 2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine (XII). Acylation of (XII) with 4-nitroben-zoic acid (XIII) by means of pyridine in either hot MeCN or DMF affords the 6-(4-nitro-benzoyl) derivative (XIV), which is reduced with H2 and Raney-Ni in MeOH to the corres-ponding 6-(4-aminobenzoyl) compound (XV). Finally, this compound is condensed with biphenyl-2-carbonyl chloride (XVI) [ obtained by treatment of biphenyl-2-carboxylic acid (V) with oxalyl chloride in CH2Cl2/DMF] by means of pyridine in acetonitrile and treated with 4N HCl.

1 Castañer, R.M.; Norman, P.; Rabasseda, X.; Leeson, P.A.; Castañer, J.; Conivaptan Hydrochloride. Drugs Fut 2000, 25, 11, 1121.
2 Yamazaki, A.; Tanaka, A.; Tsunoda, T. (Yamanouchi Pharmaceutical Co., Ltd.); Novel preparation method of condensed benzazepine derivs.. JP 1996198879 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 18505 [1,1'-biphenyl]-2-carboxylic acid 947-84-2 C13H10O2 详情 详情
(VIII) 15866 ethanimidamide C2H6N2 详情 详情
(IX) 14763 1-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one C17H17NO3S 详情 详情
(X) 41815 4-bromo-1-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one C17H16BrNO3S 详情 详情
(XI) 41816 2-methyl-6-[(4-methylphenyl)sulfonyl]-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine C19H19N3O2S 详情 详情
(XII) 41817 2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine 318237-73-9 C12H13N3 详情 详情
(XIII) 18119 4-nitrobenzoic acid; p-nitrobenzoic acid 62-23-7 C7H5NO4 详情 详情
(XIV) 41818 [2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl](4-nitrophenyl)methanone C19H16N4O3 详情 详情
(XV) 41819 (4-aminophenyl)[2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl]methanone C19H18N4O 详情 详情
(XVI) 18506 [1,1'-biphenyl]-2-carbonyl chloride C13H9ClO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

 

1 Tsunoda T, Tanaka A, et al.2004.Anew synthetic route to YM087, an argirune asopressin antagonist.Heterocycles, 63: 1113---1122
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 14763 1-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one C17H17NO3S 详情 详情
(I) 11161 methyl 2-aminobenzoate; Methyl anthranilate 134-20-3 C8H9NO2 详情 详情
(II) 66212 methyl 2-(4-methylphenylsulfonamido)benzoate   C15H15NO4S 详情 详情
(III) 66213 methyl 2-(N-(3-cyanopropyl)-4-methylphenylsulfonamido)benzoate   C19H20N2O4S 详情 详情
(IV) 66214 4-ethynyl-1-tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one   C19H17N2O3S 详情 详情
(VI) 41815 4-bromo-1-[(4-methylphenyl)sulfonyl]-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one C17H16BrNO3S 详情 详情
(VII) 41816 2-methyl-6-[(4-methylphenyl)sulfonyl]-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine C19H19N3O2S 详情 详情
(VIII) 41817 2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine 318237-73-9 C12H13N3 详情 详情
(IX) 41818 [2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl](4-nitrophenyl)methanone C19H16N4O3 详情 详情
(X) 41819 (4-aminophenyl)[2-methyl-4,5-dihydroimidazo[4,5-d][1]benzazepin-6(1H)-yl]methanone C19H18N4O 详情 详情
(XII) 18941 p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride 122-04-3 C7H4ClNO3 详情 详情
Extended Information