Triethylamine → 3-Acetylamino-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-5-(trifluoromethyl)-benzamide

HRID 1441756Notes

Reaction equation

HRID 1441756 reaction equation
[CH2:1](OP(C#N)(=O)OCC)C.C[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:21][N:20]=2)=[CH:14][C:13]=1[NH2:31].[C:32]([NH:35][C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[C:39](O)=[O:40])(=[O:34])[CH3:33].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:32]([NH:35][C:36]1[CH:37]=[C:38]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[C:39]([NH:31][C:13]1[CH:12]=[CH:17][C:16]([CH3:1])=[C:15]([NH:18][C:19]2[N:24]=[C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:22]=[CH:21][N:20]=2)[CH:14]=1)=[O:40])(=[O:34])[CH3:33]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 2868483-Acetamido-5-(trifluoromethyl)benzoic acidHCID 516892Sodium BicarbonateHCID 24820369N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

Product 1

HCID 117559093-Acetylamino-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-5-(trifluoromethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Diethylcyanophosphonate (Aldrich, Buchs, Switzerland; 0.66 mL, 4.0 mmol) is added to a stirred mixture of 4-methyl-N-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine (554 mg, 2.0 mmol), 3-acetylamino-5-(trifluoromethyl)-benzoic acid (495 mg, 2.0 mmol) and triethylamine (1.12 mL, 8.0 mmol) in 10 mL N,N-dimethylformamide at 20° C. under an argon atmosphere. After stirring for 18 hours at 20° C., the mixture is treated with saturated aqueous solution of sodium hydrogen carbonate and extracted twice with ethyl acetate. The combined extracts are dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to afford a crude product. The crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol/aqueous ammonia. The pure fractions are combined, the solvent is evaporated off under reduced pressure and the residue is crystallised from ethyl acetate-hexane to give the title compound as a cream crystalline solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined extracts are dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. customto afford a crude product
  6. customThe crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol/aqueous ammonia
  7. customthe solvent is evaporated off under reduced pressure
  8. customthe residue is crystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-30cc0a4bcb1e435e8444fde8960e1ead
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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