Cyclopropanemethanamine → HCID 72792837, compound

Participants

Reaction Steps

See FIG. 24(c). In a 50 mL round-bottomed flask 1-(2-fluoro-6-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.130 g, 0.43 mmol), cyclopropylmethanamine (0.040 g, 0.56 mmol) and TEA (0.181 mL, 1.30 mmol) was taken DCM (10 mL) under N2. To this 1-Propanephosphonic acid cyclic anhydride (0.317 g, 1.00 mmol) was added. The resulting reaction was stirred at RT for 50 min. LCMS analysis showed formation of required product. Reaction was diluted with DCM and water. DCM layer was extracted and washed with brine and dried over sodium sulphate and concentrated. Purification was done on Waters RP system to get product N-(cyclopropylmethyl)-1-(2-fluoro-6-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (0.060 g, 39.2%). ES+MS m/z: 354 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.24 (q, J=4.90 Hz, 2 H ) 0.38-0.50 (m, 2 H ) 1.03 (t, J=7.06 Hz, 1H ) 3.25 (t, J=6.22 Hz, 2 H) 3.88 (s, 3 H ) 5.47 (s, 2 H ) 6.83-6.99 (m, 2 H ) 7.26-7.46 (m, 2 H ) 8.02 (s, 1H ) 8.07 (d, J=8.10 Hz, 1 H ) 8.49 (d, J=3.96 Hz, 1 H ) 8.75 (t, J=5.65 Hz, 1 H ).

Provenance & Evidence