Ethylorthoformate → HCID 178420025, compound

Participants

Reaction Conditions

Reaction Steps

N2-(Trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)pyridine-2,3-diamine (intermediate from step 3 in example 1, 0.100 g, 0.321 mmol) was dissolved in acetic acid (10 mL) and treated with ethyl orthoformate (2.0 ml, 12.02 mmol). The solution was heated at 90° C. for 20 minutes and the solution evaporated to dryness under reduced pressure. Purification using the silica chromatography (0-10% methanol in dichloromethane gradient) gave the desired N-(trans-3-(3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)benzo[d]thiazol-2-amine (0.061 g, 0.190 mmol, 59.1% yield) as an off-white solid. M+1: 322.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.82 (ddd, J=13.89, 8.51, 4.01 Hz, 2 H) 3.20-3.32 (m, 2 H) 4.61 (tt, J=7.73, 4.01 Hz, 1 H) 5.37 (quin, J=7.68 Hz, 1 H) 7.06-7.15 (m, 1 H) 7.23-7.34 (m, 2 H) 7.61 (d, J=8.02 Hz, 1 H) 7.58 (d, J=8.22 Hz, 1 H) 8.10 (dd, J=8.12, 1.27 Hz, 1 H) 8.19 (s, 1 H) 8.41 (dd, J=4.69, 1.37 Hz, 1 H).

Provenance & Evidence