Cesium carbonate → tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

HRID 598896

Reaction equation

HRID 598896 reaction equation
[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.CS(O[CH2:21][CH2:22][C@@H:23]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][C@H:23]([NH:32][C:33](=[O:34])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:22][CH2:21][N:1]2[CH:5]=[C:4]([C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[CH:12]=[N:11][CH:10]=[CH:9]4)[CH:3]=[N:2]2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 57950570(S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonateHCID 579506126-(1H-pyrazol-4-yl)isoquinoline

Product 1

HCID 86635700tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamateYield 101.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6-(1H-pyrazol-4-yl)isoquinoline (130 mg, 0.67 mmol), (S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate (327 mg, 0.87 mmol) (prepared as shown in Scheme 15), and cesium carbonate (434 mg, 1.33 mmol) in DMF (5 mL) was stirred at room temperature for 24 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=0-40%) to provide the product as a tan solid (324 mg, 100%). LCMS (API-ES) m/z: 477 (M+H+).

Workup

  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

Sources & evidence

ORD record
ord-71a33c3e008b4353a56d03f48158d2de
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Linked notes

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