10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl isocyanate; 5-isocyanato-10,11-dihydro-5H-dibenzo[a,d]cycloheptene -Drug Synthesis Database

【结构式】

【分子编号】61662

【品名】10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl isocyanate; 5-isocyanato-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

【CA登记号】

【分子式】C₁₆H₁₃NO

【分子量】235.28536

【元素组成】C 81.68% H 5.57% N 5.95% O 6.8%

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：(XI)

Sulfonylation of pyrrole-2-carboxylic acid (VII) with 4-chloro-3-nitrobenzenesulfonyl chloride (VIII) in the presence of butyllithium leads to sulfonamide (IX). Chloride displacement in (IX) with hydrazine hydrate in refluxing THF affords the phenylhydrazine derivative (X). This is further coupled with isocyanate (XI) to produce the semicarbazide (XII). Finally, condensation of carboxylic acid (XII) with amine (VI), via activation as the mixed anhydride with isopropyl chloroformate, yields the title pyrrolecarboxamide.

参考文献中间体

合成目标

【1】 Dziadulewicz, E.K.; et al.; Nonpeptide bradykinin B2 receptor antagonists: Conversion of rodent-selective bradyzide analogues into potent, orally-active human bradykinin B2 receptor antagonists. J Med Chem 2002, 45, 11, 2160.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	61664	N~1~-(2-aminoethyl)-N~1~,N~3~,N~3~-trimethyl-1,3-propanediamine		C₈H₂₁N₃	详情	详情
(VII)	31796	Pyrrole-2-carboxylic acid; 1H-pyrrole-2-carboxylic acid	634-97-9	C₅H₅NO₂	详情	详情
(VIII)	42318	4-chloro-3-nitrobenzenesulfonyl chloride	97-08-5	C₆H₃Cl₂NO₄S	详情	详情
(IX)	61660	1-[(4-chloro-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid		C₁₁H₇ClN₂O₆S	详情	详情
(X)	61661	1-[(4-hydrazino-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid		C₁₁H₁₀N₄O₆S	详情	详情
(XI)	61662	10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl isocyanate; 5-isocyanato-10,11-dihydro-5H-dibenzo[a,d]cycloheptene		C₁₆H₁₃NO	详情	详情
(XII)	61663	1-[(4-{2-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylamino)carbonyl]hydrazino}-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid		C₂₇H₂₃N₅O₇S	详情	详情

Extended Information