Trifluoroacetic acid → HCID 70863739, compound

HRID 1403136Notes

Reaction equation

HRID 1403136 reaction equation
[F:1][CH:2]([F:36])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20]CC3C=CC(OC)=C(OC)C=3)[N:9]=2)[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=2[N:4]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>>[F:36][CH:2]([F:1])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH2:20])[N:9]=2)[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=2[N:4]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86686765HCID 86686765, compound

Product 1

HCID 70863739HCID 70863739, compoundYield 36.8%

Procedure

A mixture of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(3,4-dimethoxy benzyl)-6-(morpholin-4-yl)pyrimidin-2-amine (5.3 g) and trifluoroacetic acid (0.82 mL) was stirred at 10 for 1 hour. The reaction mixture was neutralized by the addition of saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting solid was collected by filtration and washed with diisopropyl ether to obtain 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-amine (1.36 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-01ef62d5e46044d985f5c83957913b7a
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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