Diisopropylethylamine → HCID 16116973, compound

Participants

Reaction Steps

5-(2-fluoro-5-(trifluoromethyl)benzamido)-2-methylbenzoic acid 32 (0.25 g, 0.73 mmol), HATU (0.28 g, 0.73 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.20 mL, 1.1 mmol) were taken up in DMF (6 mL). The solution was stirred at rt for 30 min then N2-phenylpyrimidine-2,5-diamine (0.105 g, 0.56 mmol) was added and the mixture was allowed to stir at rt overnight. The crude reaction mixture was taken up in minimal MeOH/DMSO and purified by preparative HPLC (acidic Gilson: 10-90% (0.1% TFA in CH3CN) in H2O over 15 min). Clean fractions were combined and allowed to stand for 2 h. Some product.TFA salt crashed out and was collected and neutralized with saturated NaHCO3 then extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated to afford 2-fluoro-N-(4-methyl-3-(((2-(phenylamino)-5-pyrimidinyl)amino)carbonyl)phenyl)-5-(trifluoromethyl)benzamide 33 as a white solid. MS m/z found 510.1 [MH+]; calc. for C26H19F4N5O2=509.15.

Provenance & Evidence