Pyridine → HCID 69557664, compound

Participants

Reaction Steps

To a suspension of 110 mg (0.30 mmol) of [[6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]acetic acid methyl ester in 3 mL of chloroform was added 0.106 mL of oxalyl chloride followed by 0.10 mL of pyridine. The reaction was stirred for 48 hours at ambient temperature then an additional 0.100 mL of oxalyl chloride and 0.100 mL of pyridine was added. This mixture was stirred and additional 4 days then quenched into solution prepared from 4 mL of water and 2 mL of concentrated ammonium hydroxide. The mixture was partitioned by the addition of 20 mL of ethyl acetate and 10 mL of water. The organic phase was dried with sodium sulfate and concentrated to 91 mg of crude solid. The residue was purified by flash chromatography (7 g of silica, ethyl acetate) to provide 69 mg (53%) of [[5-(aminooxoacetyl)-6-ethyl-7-[(3-chlorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a white solid. nmr (500 MHz, CDCl3) δ1.15 (t, J=7.4 Hz, 3H), 2.95 (q, J=7.4 Hz, 2H), 3.78 (s, 3H), 5.05 (s, 2H), 5.50 (s, 2H), 5.68 (br s, 1H), 6.60 (br s, 1H), 6.98 (d, J=7.4 Hz, 1H), 7.2 (s, 1H), 7.26 (m, 2H), 8.46 (s, 1H)

Provenance & Evidence