Sodium Carbonate → HCID 86683268、化合物

HRID 1852244ノート

反応式

HRID 1852244 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:4][N:3]=1.FC(F)(F)S(O[CH2:26][CH:27]([F:29])[F:28])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([N:14]2[CH2:19][CH2:18][N:17]([CH2:26][CH:27]([F:29])[F:28])[CH2:16][CH2:15]2)=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 71742714HCID 71742714、化合物

生成物 1

HCID 86683268HCID 86683268、化合物収率 16.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-chloro-6-methoxy-4-(piperazin-1-yl)isoquinoline (0.2 g, 0.720 mmol) in DMF (5 ml) was added 2,2-Difluoroethyl trifluoromethanesulfonate (0.154 g, 0.720 mmol) followed by sodium carbonate (0.114 g, 1.080 mmol). The reaction mass was stirred until judged complete. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to get crude compound. The crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether) to get desired compound (0.04 g, 15.93%) as semi solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.18-8.15 (d, J=12 Hz, 1H), 7.93 (s, 1H), 7.45-7.42 (d, J=12 Hz, 1H), 7.37 (s, 1H), 6.36-5.76 (tf, 1H), 3.97 (s, 3H), 3.10 (m, 4H), 2.84 (m, 4H); 19F NMR: δ ppm −118.59 (1F); MS: MS m/z 342.19 (M++1).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto get crude compound
  6. customThe crude compound was purified by silica gel chromatography (10% ethyl acetate in pet ether)

出典と根拠

ORDレコード
ord-f3fe085a3dca4bc581c59676ffa67b1f
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

読み込み中…