Dimethylamine → HCID 178494218, compound

Participants

Reaction Steps

Trans-4-(5-Bromo-6-methoxy-pyridine-3-sulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 223, 65 mg, 0.126 mmol), dimethylamine in THF (2M, 630 ul, 1.26 mmol), Pd2(dba)3 (12 mg, 0.013 mmol), X-phos (6 mg, 0.013 mmol), sodium tert-butoxide (61 mg, 0.63 mmol) were dissolved in DMF (2 ml). The reaction mixture was microwaved at 180° C. for 15 min., after which LCMS indicated the reaction was complete. The mixture was diluted with H2O and extracted with EtOAc (×3). The combined organic layers were concentrated in vacuo to a yellow oil which was purified via column chromatography using a biotage SP1, 25+M column, with 80% EtOAc in heptane as an isocratic gradient. Product containing fractions were concentrated in vacuo and repurified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA). Product containing fractions were collected and lyophilized to yield the title compound as a white solid (25.3 mg, 28%). MS MH+ 479.1

Provenance & Evidence