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

HRID 1441732Notes

Reaction equation

HRID 1441732 reaction equation
[CH3:1]CCP(=O)=O.C[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][N:16]=2)=[CH:10][C:9]=1[NH2:27].[CH2:28]([N:30]([CH2:44][CH3:45])[C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][C:32]=1[C:40]([F:43])([F:42])[F:41])[CH3:29].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:28]([N:30]([CH2:44][CH3:45])[C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:27][C:9]2[CH:8]=[CH:13][C:12]([CH3:1])=[C:11]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:18]=[CH:17][N:16]=3)[CH:10]=2)=[O:36])=[CH:33][C:32]=1[C:40]([F:43])([F:42])[F:41])[CH3:29]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 114926394-(Diethylamino)-3-(trifluoromethyl)benzoic acidHCID 16167369Propylphosphoric anhydrideHCID 24820369N-(3-amino-4-methylphenyl)-4-(pyridin-3-yl)-2-pyrimidine-amine

Product 1

HCID 117564274-Diethylamino-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-3-(trifluoromethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution containing approximately 50% of propylphosphonic anhydride in N,N-dimethylformamide (Fluka, Buchs, Switzerland; 1.14 mL, ˜1.8 mmol) is added to a stirred mixture of 4-methyl-N-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine (277.3 mg, 1 mmol), 4-diethylamino-3-(trifluoromethyl)-benzoic acid (261.3 mg, 1 mmol) and triethylamine (1.33 mL, 9.6 mmol) in 3 mL N,N-dimethylformamide. After stirring for 24 hours at room temperature, the mixture is treated with a half-saturated aqueous solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The combined organic extracts are dried (Na2SO4) and the solvent is evaporated off under reduced pressure. The crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol. The pure fractions are combined, evaporated and the residue is crystallised from acetone to give the title compound as a white solid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. customthe solvent is evaporated off under reduced pressure
  4. customThe crude product is purified by column chromatography on silica gel, eluent dichloromethane/methanol
  5. customevaporated
  6. customthe residue is crystallised from acetone

Sources & evidence

ORD record
ord-3fb706598b69452790144527d06841e0
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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