Cesium carbonate → tert-butyl(S)-3-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 598898ノート

反応式

HRID 598898 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[N:11][CH:10]=[CH:9]3)[CH:3]=[N:2]1.[F:16][C:17]([F:40])([F:39])[C:18]1[CH:38]=[CH:37][C:21]([CH2:22][C@H:23]2[CH2:27]OS(=O)(=O)[N:24]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4]3[CH:5]=[N:1][N:2]([CH2:27][C@@H:23]([NH:24][C:30](=[O:31])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:22][C:21]4[CH:37]=[CH:38][C:18]([C:17]([F:40])([F:39])[F:16])=[CH:19][CH:20]=4)[CH:3]=3)=[CH:15][CH:14]=2)[CH:9]=[CH:10][N:11]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 57634052tert-Butyl (4S)-4-(4-(trifluoromethyl)benzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 579506126-(1H-pyrazol-4-yl)isoquinoline

生成物 1

HCID 57950543tert-butyl(S)-3-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate収率 95%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of 6-(1H-pyrazol-4-yl)isoquinoline (40 mg, 0.21 mmol) (prepared as shown in Scheme 20), tert-butyl (4S)-4-[4-(trifluoromethyl)benzyl]-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (102 mg, 0.27 mmol) (prepared as shown in Scheme 1), and cesium carbonate (134 mg, 0.41 mmol) in DMF (2 mL) was stirred at room temperature for 16 hours. The mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (acetone/hexanes=0-25%) to give the product as an off-white solid (97 mg, 95%). MS (API-ES) m/z: 497 (M+H+).

後処理

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

出典と根拠

ORDレコード
ord-7ee12da9682349fab9941cad9e293372
出典データセット
uspto-grants-2011_03
特許番号
US07897619B2

反応ノート

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