Methyl acetoacetate → 5-(2,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

HRID 1593187

반응식

HRID 1593187 반응식
C[O:2][C:3](=O)[CH2:4][C:5](=O)[CH3:6].[F:9][C:10]([F:26])([F:25])[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[C:21](=O)[CH2:22]Br.[CH3:27][C:28]1([CH3:33])[CH2:30][CH:29]1[CH2:31][NH2:32].CC1(C)CC1C(N)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:48]1([NH2:54])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1>>[CH:48]1([NH:54][C:3]([C:4]2[CH:22]=[C:21]([C:12]3[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=3[C:10]([F:26])([F:25])[F:9])[N:32]([CH2:31][CH:29]3[CH2:30][C:28]3([CH3:33])[CH3:27])[C:5]=2[CH3:6])=[O:2])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1

참가 물질

7

반응물 6

HCID 7757Methyl acetoacetateHCID 7965CyclohexylamineHCID 5747172,2-DimethylcyclopropanecarboxamideHCID 21226445Aluminium lithium hydrideHCID 221379871-(2,5-Bis-trifluoromethyl-phenyl)-2-bromo-ethanoneHCID 457911891-(2,2-Dimethylcyclopropyl)methanamine

생성물 1

HCID 589990245-(2,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropylmethyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide

실험 절차

The title compound was synthesized in analogy to Example 68, using 3-oxo-butyric acid methyl ester as compound of formula R, 1-(2,5-bis-trifluoromethyl-phenyl)-2-bromo-ethanone as compound of formula S, C-(2,2-dimethyl-cyclopropyl)-methylamine (prepared from 2,2-dimethyl-cyclopropanecarboxylic acid amide by reduction with LiAlH4 according to the procedure described by Saski et al. J. Org. Chem. 1971, 36, 1968-1971) as R3—(CH2)m—NH2 and cyclohexylamine as R1R2NH, MS (ISP) 501.3 (M+H)+.

출처 및 근거

ORD 기록
ord-39b733076291469c991d814aab88bc6f
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294644B2

연결된 노트

불러오는 중…