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

HRID 598898Notes

Reaction equation

HRID 598898 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.[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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+).

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-7ee12da9682349fab9941cad9e293372
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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