Diisopropylcarbodiimide → HCID 11719945, compound

Participants

Reaction Steps

1,3-Diisopropylcarbodiimide (13.0 mg, 0.10 mmol) was added to a stirred mixture of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)benzoic acid (21 mg, 0.050 mmol), 2-amino-acetamide hydrochloride (11 mg, 0.10 mmol), 1-hydroxybenzotriazole (6.7 mg, 0.05 mmol), diisopropylethylamine (40 mg, 0.30 mmol) and 4-dimethylaminopyridine (13 mg, 0.10 mmol) in N,N-dimethylformamide (1.0 mL). The mixture was stirred at room temperature for 6 hours and then concentrated in vacuo. The resultant residue was dissolved in ethyl acetate (30 mL), washed with aqueous sodium bicarbonate solution (2×25 mL) and the organic layer was separated and concentrated. The product was purified by column chromatography over silica gel using 5% methanol in 1:1 of ethyl acetate/hexanes to give 9.6 mg (40%) of N-(2-amino-2-oxoethyl)-3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)benzamide as a white solid. MS [M+H] 481.1, 1H NMR (CDCl3) δ (ppm) 8.68 (s, 1H), 7.60-7.24 (m, 4H), 7.21 (s, 1H), 7.18-6.95 (m, 3H), 6.90 (d, J=7.8 Hz, 1H), 6.31 (b, 1H), 5.62 (b, 1H), 4.59 (t, J=6.0 Hz, 2H), 4.19, (d, J=5.1 Hz, 2H), 3.74 (t, J=6.0 Hz, 2H), 2.10 (m, 2H).

Provenance & Evidence