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

HRID 598898

Reaktionsgleichung

Reaktionsgleichung von HRID 598898
[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

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 57634052HCID 57634052, VerbindungHCID 579506126-(1H-pyrazol-4-yl)isoquinoline

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7ee12da9682349fab9941cad9e293372
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897619B2

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