Sodium hydride → (2E)-N-5-isoquinolinyl-3-[4-(trifluoromethyl)phenyl]-2-butenamide

HRID 585975노트

반응식

HRID 585975 반응식
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH3:14])=[CH:10]/[C:11]([OH:13])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][N:28]=[CH:29]2.[H-].[Na+]>C(Cl)Cl.CN(C=O)C.O>[CH:29]1[C:30]2[C:25](=[C:24]([NH:23][C:11](=[O:13])/[CH:10]=[C:9](/[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:15])=[CH:8][CH:7]=3)\[CH3:14])[CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:27][N:28]=1

참가 물질

9

반응물 4

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 707665-AminoisoquinolineHCID 287914333-[4-(Trifluoromethyl)phenyl]but-2-enoic acid

생성물 1

HCID 22032631(2E)-N-5-isoquinolinyl-3-[4-(trifluoromethyl)phenyl]-2-butenamide

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

The product from Example 142C (0.23 g, 1.00 mmol) in CH2Cl2 (5 mL) was treated with oxalyl chloride (0.15 g, 1.2 mmol), 1 drop of DMF, and stirred at ambient temperature for 45 minutes. The mixture was treated with a solution of 5-aminoisoquinoline (0.14 g, 1.0 mmol) and 98% NaH (0.048 g, 1.2 mmol) in DMF (5 mL) prepared separately by stirring for 45 minutes. The resulting mixture was stirred for 15 minutes, poured into water, and extracted with CH2Cl2. The organic phase was dried (MgSO4), evaporated, and the residue triturated with diethyl ether. The solid was dried under reduced pressure to provide the title compound. 1H NMR (300 MHz, d6-DMSO) 2.61 (s, 3H), 2.73 (s, 0.45H, DMF)), 2.89 (s, 0.45H (DMF)), 6.82 (br s, 1H), 7.70 (t, 1H), 7.83 (s, 4H), 7.95 (d, 1H), 8.04 (d, 1H), 8.21 (d, 1H), 8.56 (d, 1H), 9.33 (s, 1H), 10.20 (s, 1H); MS (ESI+) 357 (M+H)+; Elemental: Calculated for C20H15N2OF3.HCl.0.15C3H7NO: C, 66.87, H, 4.40, N, 8.20; Found: C, 66.83, H, 4.20, N, 8.27.

후처리

  1. customprepared separately
  2. stirringby stirring for 45 minutes
  3. stirringThe resulting mixture was stirred for 15 minutes
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customthe residue triturated with diethyl ether
  8. customThe solid was dried under reduced pressure

출처 및 근거

ORD 기록
ord-9453a401e02640cd84586ee729c12530
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933311B2

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