Dimethylformamide → Trifluoroacetic acid

HRID 2171364Notes

Reaction equation

HRID 2171364 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[N:11]([CH3:12])[CH:10]([CH3:13])[CH2:9][N:5]2[C:6](=[O:8])[N:7]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[O:18][C:19]1[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][C:20]=1[C:21]#[N:22].[H-].[Na+].CN(C)[CH:40]=[O:41]>>[CH3:12][N:11]1[C:4]2[N:5]([C:6](=[O:8])[N:7]=[C:2]([O:28][CH2:27][C:24]3[CH:25]=[CH:26][C:19]([O:18][C:17]4[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=[C:15]([F:14])[CH:16]=4)=[C:20]([CH:23]=3)[C:21]#[N:22])[CH:3]=2)[CH2:9][CH:10]1[CH3:13].[F:33][C:32]([F:35])([F:34])[C:40]([OH:41])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 712396162-(3-Fluoro-5-(trifluoromethyl)phenoxy)-5-(hydroxymethyl)benzonitrileHCID 867283147-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one

Product 2

HCID 6422Trifluoroacetic acidHCID 867283365-(((1,2-Dimethyl-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)-2-(3-fluoro-5-(trifluoromethyl)phenoxy)benzonitrile

Procedure

To a solution of 7-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (30 mg, 0.15 mmol) and 2-(3-fluoro-5-(trifluoromethyl)phenoxy)-5-(hydroxymethyl)be-nzonitrile (47 mg, 0.15 mmol) in N,N-dimethylformamide (DMF) (1 mL) was added NaH (12 mg, 0.30 mmol). The reaction mixture was stirred at rt for 30 min., then quenched with water. Purification via mass-directed autopreparation afforded the title product with trifluoroacetic acid salt as a white solid.

Workup

  1. customquenched with water
  2. customPurification via mass-directed autopreparation

Sources & evidence

ORD record
ord-ca6201a1a5ee448b8efa80190c524520
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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