Triethylamine → N-(cyclopropylmethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamide

Participants

Reaction Steps

See FIG. 16(b). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (200 mg, 0.67 mmol) was taken in DCM (10 mL). Added 1-Propanephosphonic acid cyclic anhydride (427 mg, 1.34 mmol) followed by the addition of Triethyl amine (339 mg, 3.35 mmol) and cyclopropylmethanamine (95 mg, 1.34 mmol). The reaction mass was stirred at RT for overnight. After the completion of the reaction added water and extracted with DCM. The organic layer was washed with water and brine solution. The organic layer was separated, dried over sodium sulphate. Evaporated the organic layer to get the residue, which was purified by column chromatography to get the pure compound. Yield-74%. ES+MS m/z: 352.38 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.02 (q, J=4.58 Hz, 2 H ) 0.18-0.31 (m, 2 H ) 0.83 (t, J=6.88 Hz, 1 H ) 2.00 (s, 3 H ) 2.98-3.11 (m, 3 H ) 3.69 (s, 3 H ) 5.43 (s, 2 H ) 7.00 (dd, J=8.29, 4.71 Hz, 1 H ) 7.68 (dd, J=8.29, 1.13 Hz, 1 H ) 7.98 (s, 1 H ) 8.17 (s, 1 H) 8.24 (dd, J=4.71, 1.13 Hz, 1 H ) 8.55 (t, J=5.75 Hz, 1 H ).

Provenance & Evidence