Water → HCID 178516970, compound

Participants

Reaction Steps

N2-(Trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-N3-cyclopropyl-5-fluoropyridine-2,3-diamine (0.051 g, 0.138 mmol) was dissolved in a mixture of dichloromethane (10 mL) and N,N-diisopropylethylamine (0.100 ml, 0.575 mmol) and cooled in an ice bath under nitrogen. Triphosgene (0.041 g, 0.138 mmol) was added in one portion. The reaction allowed to stir in the ice bath and warm to room temperature over 14 hours. Water (5 mL) and dichloromethane (10 mL) were added and the reaction stirred vigorously. The phases were separated and the organic dried with magnesium sulfate before evaporating to dryness under reduced pressure. Purification using silica chromatography (first column 0-10% methanol in dichloromethane gradient, repurify using hexane to ethyl acetate gradient) gave 3-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-1-cyclopropyl-6-fluoro-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.017 g, 0.043 mmol, 31.1% yield). M+1: 396. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.97-1.04 (m, 2 H) 1.10-1.17 (m, 2 H) 2.47-2.58 (m, 2 H) 2.88 (tt, J=6.92, 3.55 Hz, 1 H) 3.45-3.58 (m, 2 H) 4.55-4.65 (m, 1 H) 5.33 (quin, J=8.46 Hz, 1 H) 6.16 (br. s., 1 H) 7.05-7.12 (m, 1 H) 7.17 (dd, J=8.22, 2.35 Hz, 1 H) 7.25-7.35 (m, 1 H) 7.57 (d, J=8.02 Hz, 1 H) 7.60 (d, J=7.82 Hz, 1 H) 7.93 (t, J=2.15 Hz, 1 H).

Provenance & Evidence