Methylamine → HCID 68324069, compound

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Reaction Steps

In an dried round bottom flask was added 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-2-carboxylic acid (50 mg, 0.102 mmol) (Example 35), DCM (1 mL), oxalyl chloride (0.013 mL, 0.153 mmol) and DMF (10 μL). The resulting mixture was stirred at RT for 10 min. Methylamine (2M in THF) (0.256 mL, 0.511 mmol) was then added dropwise and the mixture stirred at RT for 30 min. Aqueous NaHCO3 solution (25 mL) and DCM (25 mL) were then added and the organic layer separated. The aqueous was re-extracted with DCM (2×20 mL) and the combined organics washed with brine (30 mL), dried and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-10% MeOH in DCM was followed by further purification by chromatography on silica gel, eluting with a gradient of 20-50% ethyl acetate in DCM, to give the title compound (28 mg). LCMS (A) m/z: 502 [M+1]+, Rt 1.21 min (acidic), Rt 0.91 min (basic).

Provenance & Evidence