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

反応式

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]

参加物

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード: ord-38e2fcc0283d45a5b68f1653fc06f081
出典データセット: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08367700B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 2

実験手順

後処理

出典と根拠

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