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

HRID 887244ノート

反応式

HRID 887244 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.HCl0.15C3H7NO: C, 66.87; H, 4.40; N, 8.20. Found: C, 66.83; H, 4.20; N, 8.27.

後処理

  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

出典と根拠

ORDレコード
ord-9a53bb2509ee4fa78694bfed69b51d08
出典データセット
uspto-grants-2012_08
特許番号
US08247413B2

反応ノート

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