HCID 178493980, compound → HCID 178493981, compound

Participants

Reaction Steps

To a 15-mL round-bottomed flask was added 7-chloro-N-(−3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)quinoxalin-2-amine (example 19, 118 mg, 0.310 mmol) and palladium on activated carbon (10 wt. %, 33.0 μl, 0.310 mmol) in methanol. The reaction mixture was stirred under a hydrogen balloon for 3 days. The solution was filtered and concentrated in vacuo to give the crude material as a yellow oil. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (4 g, 0-20% (2M ammonia in methanol) in dichloromethane gradient) to provide N-(trans-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)-3,4-dihydroquinoxalin-2-amine (80 mg, 0.230 mmol, 74.1% yield) as light-yellow glass. M+1: 349.1. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.68 (br. s, 1 H) 2.52 (d, J=2.05 Hz, 2 H) 3.33-3.52 (m, 2 H) 3.81 (s, 2 H) 4.25 (s, 3 H) 4.68-4.81 (m, 1 H) 5.40 (quin, J=8.59 Hz, 1 H) 6.58 (dd, J=7.53, 1.39 Hz, 1 H) 6.76 (td, J=7.50, 1.60 Hz, 1 H) 6.84 (td, J=7.50, 1.60 Hz, 1 H) 7.05 (d, J=7.16 Hz, 1 H) 7.10 (dd, J=7.82, 5.04 Hz, 1 H) 7.75 (dd, J=7.82, 1.39 Hz, 1 H) 8.16 (dd, J=4.97, 1.46 Hz, 1 H).

Provenance & Evidence