Triethylamine → HCID 90466854, compound

Participants

Reaction Steps

See FIG. 21(b). In a 25 mL thermal vial was charged with 1-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (100 mg, 0.27 mmol) and HATU (125 mg, 0.33 mmol) were taken in NMP (4 mL) and stirred for 10 min at rt. Then (S)-2-fluoropropan-1-amine hydrochloride (37.3 mg. 0.33 mmol) and triethyl amine (0.114 mL, 0.82 mmol) were added and stirred for 1 h at RT. The LCMS showed completion of the reaction. The reaction mixture was poured into water and extracted with chloroform. The organic layer was dried and concentrated and crude was submitted to reverse phase purification. The pure fractions were concentrated to get (S)—N-(2-fluoropropyl)-1-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (82 mg, 70.6%) a solid. ES+MS m/z: 425 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.15-1.44 (m, 3 H ) 2.44 (s, 3 H ) 3.39-3.79 (m, 2 H ) 3.98 (s, 3 H ) 4.75 (td, J=6.50, 3.39 Hz, 1 H ) 4.92 (td, J=6.50, 3.20 Hz, 1 H ) 5.48 (s, 2 H ) 7.81 (d, J=2.26 Hz, 1 H ) 7.91-8.03 (m, 1H) 8.25 (s, 1 H ) 8.34-8.42 (m, 1 H ) 8.53-8.62 (m, 1 H ) 8.90 (t, J=5.93 Hz, 1 H ).

Provenance & Evidence