Citric Acid → N-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoyl)-methanesulfonamide

Participants

Reaction Steps

A solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid [100 mg, 0.26 mmol, Example 35(a)], methanesulfonamide (38 mg, 0.4 mmol), and dimethyl-pyridin-4-yl-amine (64 mg, 0.53 mmol) in DCM (5 mL) is treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (101 mg, 0.53 mmol). After 8 hours at 20° C., the mixture is diluted with water, acidified (pH2 with citric acid), and extracted with DCM. The extracts are dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica gel eluting with 10% MeOH in DCM to afford N-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoyl)-methanesulfonamide [53 mg, 45%, Example 25(a)]. LCMS: RT=2.35 minutes, MS: 457 (M+H). 1H NMR (300 MHz, CDCl3), □8.3 (1H, s), 8.08 (1H, brs), 7.9 (1H, d, J=4.8 Hz), 7.34 (1H, brs), 7.12 (2H, d, J=8.4 Hz), 6.82 (2H, d, J=8.4 Hz), 6.46 (1H, brs), 6 (1H, brs), 3.91 (3H, s), 3.76 (3H, s), 3.61 (2H, brs), 3.31 (3H, s), 2.86 (2H, t, J=6.9 Hz).

Provenance & Evidence