1H-Indole-2-carboxylic acid, 1-methyl- → HCID 16116975, compound

Participants

Reaction Steps

In a 16×120 mm resealable pyrex tube, 1-methyl-1H-indole-2-carboxylic acid (0.11 g, 0.62 mmol), HATU (0.24 g, 0.62 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.17 ml, 0.96 mmol) were taken up in DMF (5 mL) and allowed to stir at rt for 30 min. 5-amino-2-methyl-N-(2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)benzamide 30 (0.200 g, 0.48 mmol) was added and the mixture was stirred at rt overnight. The crude reaction mixture was taken up in minimal MeOH/DMSO and purified by preparative HPLC (acidic Shimadzu: 15-85% (0.1% TFA in CH3CN) in H2O over 20 min). Clean fractions were combined and neutralized with saturated NaHCO3 then extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated to afford 1-methyl-N-(4-methyl-3-((2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)carbamoyl)phenyl)-1H-indole-2-carboxamide 31 as a tan solid. MS m/z found 575.2 [MH+]; calc. for C33H34N8O2=574.28.

Provenance & Evidence