Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-Methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid | HCID 10402880 | — |
| Reactant | HCID 58902253 | HCID 58902253 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67214549 | HCID 67214549 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07169791B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-2165b62194074c08aa6a2bbfd0d890a7 |
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| Source note | uspto-grants-2007_01 |
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