Trimethyl orthoformate → HCID 25214475, compound

Participants

Reaction Steps

A mixture of 1-(2-(1,2,3,4-tetrahydroisoquinolin-5-yloxy)pyridin-3-yl)-3-(4-(trifluoromethoxy)phenyl)urea (238f, 15 mg, 0.034 mmol), cyclohexanecarboxaldehyde (38 mg, 034 mmol), acetic acid (50 μL) were added to NMP (0.75 mL) and trimethylorthoformate (0.5 mL) and stirred at rt for 2.5 h. Triacetoxyborohydride (36 mg) was added and stirring was continued for 18 h. A solution of acetic acid in methanol (50% v/v, 0.5 mL) was added and reation mixture was directly purified on preparative HPLC to yield the desired material (5.4 mg). (M+H)+=541. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.6-1.9 (m, 10H), 2.32 (m, 1H), 3.04-3.06 (m, 2 H), 3.66-3.75 (m, 2 H), 4.31-4.43 (m, 2 H), 4.60-4.70 (m, 2 H), 7.11 (dd, J=7.83, 4.80 Hz, 1 H), 7.18 (t, J=7.83 Hz, 2 H), 7.33 (d, J=8.08 Hz, 2 H), 7.39 (t, J=7.83 Hz, 1 H), 7.56 (d, J=9.09 Hz, 2 H), 7.65 (dd, J=4.80, 1.76 Hz, 1H), 8.53 (d, J=7.84 Hz, 1 H), 8.78 (s, 1 H), 9.54 (s, 1 H).

Provenance & Evidence