Water → HCID 58344991, compound

Participants

Reaction Steps

3-(3-(4-(aminomethyl)phenyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine HCl salt (63 mg, 0.2 mmol) was suspended in dichloromethane (2 mL). Diisopropylethylamine (0.07 mL, 0.4 mmol) was added. After everything went into solution 1-tert-butyl-4-isocyanatobenzene (32 mg, 0.2 mmol) were added. After 20 min water (10 mL) was added and diluted with dichloromethane (10 mL). The organic phase was separated and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and it was purified by silica gel chromatography (0-20% methanol in dichloromethane) to yield the desired product (14 mg, 15% yield). Mp. 210-212° C.; 400 M Hz 1H NMR (CD3OD) δ: 8.32 (dd, J=0.8 Hz and 2.4 Hz, 1H), 8.19 (dd, J=0.6 Hz and 3.8 Hz, 1H), 7.98-7.94 (m, 1H), 7.55-7.49 (m, 2H), 7.45-7.37 (m, 3H), 7.35-7.24 (m, 5H), 6.48-6.23 (m, 1H), 4.48 (s, 2H), 1.29 (s, 9H); LCMS [M+H]: 492.

Provenance & Evidence