1,2-Dichloroethane → n-[4-({[2-(2,4-Dichlorophenoxy)phenyl]amino}sulfonyl)phenyl]pyrimidine-5-carboxamide

Participants

Reaction Steps

To a solution of the compound of Step 2 (0.1 g, 0.244 mmol), pyrimidin-5-carboxylic acid (0.03 g, 0.244 mmol) HOAT (0.033 g, 0.244 mmol) and EDC (0.047 g, 0.244 mmol) in DMF (1 mL) at room temperature was added triethylamine (0.068 mL, 0.489 mmol). After 18 hr pyrimidin-5-carboxylic acid (0.03 g, 0.244 mmol) HOAT (0.033 g, 0.244 mmol), EDC (0.047 g, 0.244 mmol) and triethylamine (0.068 mL, 0.489 mmol) were added. The reaction mixture was stirred for a further 16 hr, diluted with DME (2 mL), treated with trifluoroacetic acid, and purified directly by reverse phase HPLC waters Prepak C-18 column eluting with 5-95% CH3CN: water containing 0.1% TPA. The pure fractions were combined and lyophilized to afford the title compound. C23H16Cl2N4O4S MH+ requires 515.0342 found 515.0349. Proton NMR (400 MHz, CDCl3) δ 6.53 (d, J=8.8 Hz, 1H), 6.62 (d, J=8.2 Hz), 7.00-7.10 (m, 3H), 7.14 (t, J=7.8 Hz, 1H), 7.41 (d, J=2.5 Hz, 1H), 7.64(d, J=8.6 Hz, 2H), 7.70-7.80 (m, 3H), 8.03(s, 1H), 9.28 (s, 2H), 9.43 (s, 1H).

Provenance & Evidence