Pyridine → HCID 69558262, compound

Participants

Reaction Steps

To a suspension of 140 mg (0.407 mmol) of [[6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester in 5 mL of chloroform was added 0.053 mL of oxalyl chloride followed by 0.10 mL of pyridine. The reaction was stirred for 30 hours at ambient temperature then an additional 0.10 mL of oxalyl chloride was added. This mixture was stirred and additional 2 days then quenched into 4.0 mL of dilute ammonium hydroxide. The product was extracted into 4.0 mL of methylene chloride. The organic phase was washed with saturated sodium chloride, dried with sodium sulfate and concentrated to 300 mg of crude oil. The residue was purified by flash chromatography (30 g of silica, hexanes-ethyl acetate gradient 100:0 to 25:75) to provide 28 mg (17%) of [[5-(aminooxoacetyl)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a solid. nmr (300 MHz, CDCl3) δ1.20 (t, 3H), 2.88 (q, 2H), 3.70 (s, 3H), 4.98 (s, 2H), 5.44 (s, 2H), 6.00 (s, 1H), 6.60 (s, 1H), 6.84 (m, 2H), 6.90 (dt, 1H), 7.20 (dt, 1H), 8.39 (s, 1H)

Provenance & Evidence