Acetaldehyde → HCID 73505015, compound

Participants

Reaction Steps

A solution of (R)-1-(3-amino-4-(methoxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (34.8 mg, 0.102 mmol) in chloroform (0.6 ml) and MeOH (0.3 ml) was charged with MgSO4 (45 mg, 0.374 mmol), TFA (24 μl, 0.312 mmol) and acetaldehyde (0.02 ml, 0.354 mmol). The mixture was stirred at RT for 1 hr, then charged with sodium cyanoborohydride (22 mg, 0.350 mmol) before it was stirred at RT for 1.5 hr. The mixture was filtered to remove insoluble matter, rinsing with MeOH and DCM and concentrated in vacuo. The residue was purified by mass-triggered reverse-phase HPLC to provide (R)-1-(3-(ethylamino)-4-(methoxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd for C19H25N6O2 [M+H]+ 369. found 369. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 11.64 (s, 1H), 8.96 (s, 1H), 7.33 (m, 4H), 7.23 (m, 1H), 7.15 (s, 1H), 5.56 (t, J=6.5 Hz, 1H), 4.85 (t, J=7.3 Hz), 4.63 (m, 2H), 3.32 (s, 3H, overlaps with H2O peak), 3.22 (m, 2H), 1.39 (d, 6.8 Hz, 3H), 1.20 (t, J=4.9 Hz, 3H).

Provenance & Evidence