Triethylamine → HCID 67214549, compound

HRID 2099441Notes

Reaction equation

HRID 2099441 reaction equation
C(OP([C:9]#[N:10])(=O)OCC)C.[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][C:13]=1[NH:21][C:22]1[N:27]=[C:26]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:25]=[CH:24][N:23]=1.[OH:34][C:35]([C:38]1[CH:39]=[C:40](N)[CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)([CH3:37])[CH3:36].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH:10][CH2:9][C:40]2[CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=[C:38]([C:35]([OH:34])([CH3:37])[CH3:36])[CH:39]=2)=[O:17])=[CH:14][C:13]=1[NH:21][C:22]1[N:27]=[C:26]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH:25]=[CH:24][N:23]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 104028804-Methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acidHCID 58902253HCID 58902253, compound

Product 1

HCID 67214549HCID 67214549, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Diethylcyanophosphonate (Aldrich, Buchs, Switzerland; 0.33 mL, 2.0 mmol) is added to a stirred mixture of 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzoic acid (306 mg, 1.0 mmol), 3-[(1-hydroxy-1-methylethyl)]-5-(1,1,1-trifluoromethyl)benzeneamine (220 mg, 1.0 mmol) and triethylamine (560 μL, 4.0 mmol) in 5 mL N,N-dimethylformamide at 10° C. After stirring for 3 hours at 60° C., the mixture is treated with saturated aqueous solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The combined extracts are dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to afford a crude product which is recrystallised from ethylacetate to give the title compound as a crystalline solid, m.p. 253-258° C.

Workup

  1. extractionextracted three times 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 which
  6. customis recrystallised from ethylacetate

Sources & evidence

ORD record
ord-373f22d53a3d427ca38c8458e334cfbd
Source dataset
uspto-grants-2009_08
Patent number
US07569566B2

Reaction notes

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