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

HRID 598898노트

반응식

HRID 598898 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7ee12da9682349fab9941cad9e293372
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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