Dimethyl Sulfoxide → HCID 178516971, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-5-bromo-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 82, 0.128 g, 0.355 mmol) and DMSO (2 mL). N,N-Diisopropylethylamine (0.250 ml, 1.437 mmol) was added followed by 2-chlorobenzothiazole (0.060 ml, 0.461 mmol) and the reaction mixture was sealed under argon and heated at 100° C. for 24 h. The reaction mixture was diluted with water and a small amount of MeOH. The resultant solid was filtered, washed with water and dried in vacuo to give 94 mg (58%) of an off-white crystalline solid. ESI MS 456.8, 458.8 [M+1]. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.53 (d, J=6.28 Hz, 1 H), 8.16 (s, 1 H), 7.63-7.75 (m, 1 H), 7.42 (d, J=7.45 Hz, 1 H), 7.15-7.30 (m, 1 H), 6.96-7.09 (m, 1 H), 5.12 (quin, J=8.29 Hz, 1 H), 4.41-4.65 (m, 1 H), 3.14-3.29 (m, 2 H), 2.87-3.01 (m, 1 H), 2.39-2.57 (m, 2 H), 0.91-1.11 (m, 4 H)

Provenance & Evidence