Triethylamine → HCID 90466564, compound

Participants

Reaction Steps

See FIG. 16(a). 1-(1-(2,6-difluorophenyl)ethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.090 g, 0.30 mmol), 2-fluoroethanamine (0.019 g, 0.30 mmol) and triethylamine (0.166 mL, 1.19 mmol) was taken in DCM (15 mL) under N2 and stirred. After 5 min, 1-Propanephosphonic acid cyclic anhydride (0.379 g, 1.19 mmol) was added. The resulting reaction was stirred at rt for 40 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 1-(1-(2,6-difluorophenyl)ethyl)-N-(2-fluoroethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (0.040 g, 38.7%) as a solid. ES+MS m/z: 348.40. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.05 (d, J=6.97 Hz, 3 H ) 3.67 (q, J=5.21 Hz, 1 H ) 3.71-3.82 (m, 1 H ) 4.49 (t, J=4.90 Hz, 1 H ) 4.65 (t, J=4.99 Hz, 1 H ) 6.22 (q, J=7.16 Hz, 1 H ) 7.13 (t, J=8.57 Hz, 2 H ) 7.29 (dd, J=8.48, 4.71 Hz, 1 H ) 7.34-7.52 (m, 1 H ) 7.80 (d, J=8.29 Hz, 1 H ) 8.41 (s, 1 H ) 8.50 (d, J=4.71 Hz, 1 H) 8.92 (t, J=5.75 Hz, 1 H ).

Provenance & Evidence