Cesium fluoride → HCID 86691823, compound

HRID 1616216Notes

Reaction equation

HRID 1616216 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:27])=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH3:26])[C:17](=[O:25])[N:18]([CH2:19][C@H:20]4[CH2:22][C:21]4([F:24])[F:23])[C:13]3=[CH:12][CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2].[F-].[Cs+].C[Si](C)(C)[C:32]([F:35])([F:34])[F:33]>CN(C=O)C.CO>[F:24][C:21]1([F:23])[CH2:22][CH:20]1[CH2:19][N:18]1[C:13]2[C:14](=[N:15][C:10]([C:8]3[CH:9]=[C:4]([C:1]([OH:3])([CH3:2])[C:32]([F:35])([F:34])[F:33])[CH:5]=[CH:6][C:7]=3[CH3:27])=[CH:11][CH:12]=2)[N:16]([CH3:26])[C:17]1=[O:25]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 86691824HCID 86691824, compound

Product 1

HCID 86691823HCID 86691823, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a microwave vial, 5-(5-acetyl-2-methylphenyl)-1-{[(1R)-2,2-difluorocyclopropyl]methyl}-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (9-4) (25 mg, 0.067 mmol) and Cesium fluoride (21 mg, 0.135 mmol) were dissolved in DMF (0.35 mL). Trimethyl(trifluoromethyl)silane (54 uL, 0.34 mmol) was added dropwise and allowed to stir at room temperature for 30 minutes. The mixture was diluted with methanol and purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile); the desired fractions were collected and concentrated to produce racemic 1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-[2-methyl-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (10-1). HRMS (M+H)+: observed=442.1543, calculated=442.1548.

Workup

  1. custompurified
  2. customthe desired fractions were collected
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-73117c9f120a4d9988d5db56fddea150
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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