Acetic Acid → 4-(4-Cyclopropylmethyl-piperazin-1-yl)-6-(trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt

HRID 2053078Notes

Reaction equation

HRID 2053078 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N:8]1([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22](C(F)(F)F)[CH:21]=3)[N:17]=[C:16]([C:30]#[N:31])[N:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH:32]1([CH:35]=O)[CH2:34][CH2:33]1.C(O)(=O)C.C([BH3-])#N>CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:32]1([CH2:35][N:11]2[CH2:10][CH2:9][N:8]([C:14]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:2]([F:7])([F:6])[F:1])[N:17]=[C:16]([C:30]#[N:31])[N:15]=3)[CH2:13][CH2:12]2)[CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 498716Cyano-borohydrideHCID 866124954-(Piperazin-1-yl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt

Product 1

HCID 866124984-(4-Cyclopropylmethyl-piperazin-1-yl)-6-(trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 4-(piperazin-1-yl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt (67 mg) in methanol (2 ml) was added cyclopropane carboxaldehyde (13 μl), acetic acid (0.5 ml) and resin-bound cyanoborohydride (1 mmol/g, 89 mg). The reaction mixture was stirred at room temperature for 16 hrs. Resin was filtered off and the filtrate was concentrated in vacuo. The residue was dissolved in methanol and purified using the prep-HPLC to give 4-(4-cyclopropylmethyl-piperazin-1-yl)-6-(trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt as a white solid (10 mg).

Workup

  1. filtrationResin was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol
  4. custompurified

Sources & evidence

ORD record
ord-9764b3c827ba4473b185c6b3ab682603
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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