Dimethylformamide → Water TFA acetonitrile

HRID 2247422Notes

Reaction equation

HRID 2247422 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20]C)=[O:19])[CH:13]=2)=[CH:8][C:4]=1[C:5](O)=[O:6].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.C(P(=O)(OCC)[O:37]CC)#N.C(N(CC)CC)C.CN(C)[CH:53]=[O:54]>C(OCC)(=O)C>[OH2:2].[C:28](#[N:29])[CH3:27].[F:22][C:23]([F:33])([F:32])[C:53]([OH:54])=[O:37].[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[C:18]([OH:20])=[O:19])=[CH:8][C:4]=1[C:5]([NH:29][CH2:28][C:27]1[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:32])[F:33])=[CH:31][CH:30]=1)=[O:6]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 768044-(Trifluoromethyl)benzylamineHCID 59218967HCID 59218967, compound

Product 2

HCID 22145617Water TFA acetonitrileHCID 59218923HCID 59218923, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

12 mg of 2-Methoxy-5-[3-(methoxycarbonyl)phenyl]benzoic acid and 9 mg of 4-trifluoromethylbenzylamine were dissolved in 0.2 ml of N,N-dimethylformamide, 9 ml of diethyl cyanophosphonate and 50 ml of triethylamine were added thereto, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture which was then washed with water. The organic layer was evaporated, and the residue was dissolved in 0.4 ml of ethanol. 0.1 ml of 5N sodium hydroxide was added thereto, and the mixture was stirred at room temperature for 1 hour. 1 N hydrochloric acid was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was evaporated, and the residue was purified by HPLC using a reverse phase system column and a water-acetonitrile-trifluoroacetic acid eluent, to give the title compound.

Workup

  1. washwas then washed with water
  2. customThe organic layer was evaporated
  3. dissolutionthe residue was dissolved in 0.4 ml of ethanol
  4. addition0.1 ml of 5N sodium hydroxide was added
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. addition1 N hydrochloric acid was added to the reaction mixture which
  7. extractionwas then extracted with ethyl acetate
  8. customThe organic layer was evaporated
  9. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-74cf0548c329468696dc40461e08b348
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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