6-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride → n-[2-Chloro-6-methyl-4-(6-trifluoromethyl-3,4-dihydro-1h-isoquinolin-2-yl)-phenyl]-3,3-dimethylbutanamide

HRID 2067812노트

반응식

HRID 2067812 반응식
CC(C)([O-])C.[K+].Cl.[F:8][C:9]([F:21])([F:20])[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][NH:15][CH2:14][CH2:13]2.Br[C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([NH:30][C:31](=[O:37])[CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[C:25]([Cl:38])[CH:24]=1>C1(C)C=CC=CC=1>[Cl:38][C:25]1[CH:24]=[C:23]([N:15]2[CH2:14][CH2:13][C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:9]([F:8])([F:20])[F:21])[CH:11]=3)[CH2:16]2)[CH:28]=[C:27]([CH3:29])[C:26]=1[NH:30][C:31](=[O:37])[CH2:32][C:33]([CH3:35])([CH3:34])[CH3:36]

참가 물질

5

반응물 3

HCID 217125586-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 23665647Potassium tert-butoxideHCID 58097339N-(4-bromo-2-chloro-6-methylphenyl)-3,3-dimethylbutanamide

생성물 1

HCID 24937205n-[2-Chloro-6-methyl-4-(6-trifluoromethyl-3,4-dihydro-1h-isoquinolin-2-yl)-phenyl]-3,3-dimethylbutanamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (197 mg, 1.75 mmol), 6-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (154 mg, 0.65 mmol) and N-(4-bromo-2-chloro-6-methyphenyl)-3,3-dimethylbutanamide (200 mg, 0.63 mmol) were then added and the reaction mixture was stirred at 90° C. overnight. The reaction mixture was then cooled to room temperature, concentrated and purified by thin layer chromatography (dichloromethane:methanol 5%) to afford the title compound as a solid.

후처리

  1. stirringthe reaction mixture was stirred at 90° C. overnight
  2. concentrationconcentrated
  3. custompurified by thin layer chromatography (dichloromethane:methanol 5%)

출처 및 근거

ORD 기록
ord-8fb6f923c8c84c5dbc72a5bae1c3818e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293911B2

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