Acetonitrile → HCID 57518506, compound

HRID 874760Notes

Reaction equation

HRID 874760 reaction equation
[H-].[Na+].[N:3]1[NH:4][CH:5]=[C:6]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:7]=12.[CH:18]1([S:21](Cl)(=[O:23])=[O:22])[CH2:20][CH2:19]1.[C:25](#N)[CH3:26]>>[CH:18]1([S:21]([N:4]2[CH:5]=[C:6]3[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:7]3=[N:3]2)(=[O:23])=[O:22])[CH2:26][CH2:25][CH2:19][CH2:20]1.[CH:18]1([S:21]([N:3]2[C:7]3[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:6]=3[CH2:5][NH:4]2)(=[O:23])=[O:22])[CH2:26][CH2:25][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 2760919Cyclopropanesulfonyl chlorideHCID 178451520HCID 178451520, compound

Product 2

HCID 57518506HCID 57518506, compoundHCID 67036470HCID 67036470, compound

Procedure

To a suspension of sodium hydride (60% dispersion in oil, 1.55 g, 38.7 mmol) in anhydrous acetonitrile (200 mL) was added to tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (5.3 g, 25.5 mmol) in one portion under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 2 h. To the resulting white suspension was slowly added cyclopropanesulfonyl chloride (6.9 g, 49.1 mmol) and the mixture was stirred at room temperature for 18 h, quenched with water (120 mL) and the layers were separated. The aqueous layer was then extracted with dichloromethane (2×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified on silica chromatography (300 g Biotage™ column) and eluted with 15-80% ethyl acetate in hexanes to yield the title compound and tert-butyl 1-(cyclopentylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate as a white solid. LC/MS: 314.2 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. customquenched with water (120 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was then extracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified on silica chromatography (300 g Biotage™ column)
  8. washeluted with 15-80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4240f4d3f91e4c1f9980671607500074
Source dataset
uspto-grants-2015_03
Patent number
US08980929B2

Reaction notes

Loading…