Water → HCID 121393761, compound

HRID 1480031Notes

Reaction equation

HRID 1480031 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7](=[O:19])[NH:6][C:5]=1[C:20]1[N:24]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[N:23]=[CH:22][CH:21]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O>CN(C=O)C>[CH3:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7](=[O:19])[N:6]([S:34]([CH3:33])(=[O:36])=[O:35])[C:5]=1[C:20]1[N:24]([C:25]2[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[CH:31][CH:32]=2)[N:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 121393736HCID 121393736, compound

Product 1

HCID 121393761HCID 121393761, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (12 mg of a 60% dispersion in mineral oil, 0.30 mmol) was added to a solution of 4-(5-{5-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (Example 1) (94 mg, 0.23 mmol) in DMF (1.5 mL) under a nitrogen atmosphere. The mixture was stirred for 5 minutes and the resultant yellow solution was treated with methanesulfonyl chloride (32 mg, 21.4 μL, 0.28 mmol). The mixture was stirred for 2 h then treated with water and extracted with EtOAc. The organic phase was washed with water and brine then dried (sodium sulfate) and concentrated in vacuo. T he residue was purified by chromatography using silica gel eluting with 25%-60% ethyl acetate in cyclohexane. The product thus obtained was freeze-dried from acetonitrile-water to afford the title compound (54 mg) a white solid.

Workup

  1. stirringThe mixture was stirred for 2 h
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialthen dried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customT he residue was purified by chromatography
  7. customThe product thus obtained
  8. dry with materialwas freeze-dried from acetonitrile-water

Sources & evidence

ORD record
ord-81a8592db18049d0b427e4b89e61f09d
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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