1,2,3,4-Tetrahydro-1-phenylisoquinoline → 4-oxo-4-(1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-(trifluoromethyl)benzyl)butyric acid amide

HRID 383994

반응식

HRID 383994 반응식
N=C=N.[C:4]1([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][NH:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:20]=[C:21]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)[CH2:22][CH2:23][C:24](O)=[O:25].C(Cl)Cl.CCO>C(Cl)Cl.CN(C=O)C>[O:25]=[C:24]([N:11]1[CH2:12][CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:23][CH2:22][C:21]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:37])[F:38])[CH:30]=1)=[O:20]

참가 물질

7

반응물 4

HCID 1001371,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 160435CarbodiimideHCID 21584144Dichloromethane ethanolHCID 433971044-Oxo-4-(3-(trifluoromethyl)benzylamino)butyric acid

생성물 1

HCID 462139164-oxo-4-(1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-(trifluoromethyl)benzyl)butyric acid amide수율 62%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

1.98 g (˜2.0 mmol) of PS carbodiimide resin were added to a solution of 209 mg (1.0 mmol) of 1-phenyl-1,2,3,4-tetrahydroisoquinoline and 275 mg (1.0 mmol) of 4-oxo-4-(3-(trifluoromethyl)benzylamino)butyric acid (intermediate VVV01) in a mixture of DCM and DMF (82 ml, 40:1 vv) and the mixture was shaken for 16 h at RT. Then the resin was filtered off and it was washed with DCM and MeOH. The filtrate was concentrated to small volume under vacuum. Column chromatography (DCM/EtOH 40:1) of the residue produced 287 mg (0.6 mmol, 62%) of 4-oxo-4-(1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-(trifluoromethyl)benzyl)butyric acid amide. MS: m/z 467.2 [M+H]+.

후처리

  1. filtrationThen the resin was filtered off
  2. washit was washed with DCM and MeOH
  3. concentrationThe filtrate was concentrated to small volume under vacuum

출처 및 근거

ORD 기록
ord-38e2fcc0283d45a5b68f1653fc06f081
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367700B2

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