Methylamine → HCID 57635858, compound

Participants

Reaction Steps

To a solution 2-{[3-(1,1-dimethylpropyl)-1-(3-fluoro-2-methoxyphenyl)-1H-pyrazol-5-yl]amino}nicotinic acid, (Example 140, synthesized in a manner similar to that of Example 8, 50 mg, 0.13 mmol) in CH3CN (1 mL) was added 1 drop of dimethyl formamide followed by oxalyl chloride (9 μL, 0.13 mmol). The mixture was stirred at rt for 1 h, followed by addition of methyl amine (16 μL of a 40% solution in water, 0.25 mmol). The mixture was again stirred at rt for 1 h and concentrated to dryness. The residue was dissolved in methanol (1 mL), filtered through an octyl solid phase extraction tube and subjected to HPLC purification with a gradient elution from 10% to 90% acetonitrile in water to afford 33 mg (70%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 8.30 (d, 1H), 8.23 (s, 1H), 7.50 (d, 1H), 7.15-7.30 (m, 3H), 6.80 (t, 1H), 6.60 (s, 1H), 3.77 (s, 3H), 2.95 (br s, 6H), 1.70 (q, 2H), 1.32 (s, 6H), 0.85 (t, 3H). ES-MS m/z 426.2 (MH+); HPLC RT (min) 3.57.

Provenance & Evidence