Diisopropylethylamine → HCID 178516974, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 0.133 g, 0.472 mmol), 2-chloro-1,5-naphthyridine (0.100 g, 0.608 mmol) and DMSO (2 mL). N,N-Diisopropylethylamine (0.250 mL, 1.437 mmol) was added and the reaction mixture was sealed under argon and heated at 100° C. for 59 h. The reaction was cooled to room temperature and partitioned between water/DCM. The aqueous layer was extracted with DCM (3×) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco, (25 gram)) eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→1:19) to give 67 mg (34%) of a white crystalline solid. ESI-MS 374.0 [M+1]. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (dd, J=4.30, 1.56 Hz, 1 H), 8.00 (d, J=3.33 Hz, 1 H), 7.97 (d, J=3.33 Hz, 1 H), 7.93 (d, J=9.19 Hz, 1 H), 7.81-7.89 (m, 2 H), 7.46 (dd, J=8.41, 4.11 Hz, 1 H), 7.02 (d, J=9.19 Hz, 1 H), 5.21 (m, 1 H), 4.64-4.76 (m, 1 H), 3.25-3.38 (m, 2 H), 2.91-3.02 (m, 1 H), 2.34-2.45 (m, 2 H), 0.94-1.11 (m, 4 H)

Provenance & Evidence