Water → HCID 121393749, compound

HRID 1480024Notes

Reaction equation

HRID 1480024 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.[C:33](Cl)(=[O:35])[CH3:34].O>C1COCC1>[C:33]([N:6]1[C:5]([C:20]2[N:24]([C:25]3[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[CH:31][CH:32]=3)[N:23]=[CH:22][CH:21]=2)=[C:4]([CH3:3])[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]1=[O:19])(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 121393736HCID 121393736, compound

Product 1

HCID 121393749HCID 121393749, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (12.5 mg of a 60% dispersion in mineral oil, 0.31 mmol) was added to a stirred suspension 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) (102 mg, 0.25 mmol) in THF (5.0 mL) under a nitrogen atmosphere. This resulted in degassing and the formation of a yellow solution. Acetyl chloride (0.022 mL, 0.5 mmol) was added and the mixture was stirred for 1 h then left to stand for 16 h. Water (10 mL) was added and the mixture was extracted with EtOAc (2×10 mL). The combined organic phase was dried (sodium sulfate) and concentrated in vacuo. The residue was purified by flash column chromatography (2 g Si II SPE eluted with DCM then 10% EtOAc in DCM). Concentration of the appropriate fractions in vacua gave the title compound which was freeze-dried from acetonitrile/water to afford a fluffy white solid (56 mg).

Workup

  1. customThis resulted
  2. customin degassing
  3. waitthen left
  4. waitto stand for 16 h
  5. extractionthe mixture was extracted with EtOAc (2×10 mL)
  6. dry with materialThe combined organic phase was dried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (2 g Si II SPE
  9. washeluted with DCM

Sources & evidence

ORD record
ord-dde4f3c5f6ff4c22be6f910c0e3bf748
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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