Diisopropylethylamine → HCID 178461953, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-((S)-1-aminoethyl)-5-fluoro-3-pyridin-2-yl-3H-benzoimidazole-4-carbonitrile dihydrochloride (250 mg, 0.71 mmol) in IPA (7 mL) was added 6-chloro-9-(tetrahydro-pyran-2-yl)-9H-purine (220 mg, 0.92 mmol) and DIPEA (361 μL, 2.1 mmol) and the reaction mixture heated at 90° C. for 16 h. The reaction mixture was concentrated in vacuo and the resultant residue subjected to flash chromatography (SiO2, eluting with 0-10% methanol in EtOAc). LCMS (Method C): RT=2.86 min, [M+H]+=484. The product was dissolved HCl in methanol (5 mL, 2.5M) and the reaction stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the resultant residue loaded onto an SCX 2 cartridge, washed with methanol then eluted with ammonia in methanol (2M). The eluent was concentrated in vacuo and the residue triturated with diethyl ether to give 290 as a white solid (174 mg, 51%) 1H NMR 400 MHz (DMSO-d6): δ 12.57 (1H, br s), 8.53-8.50 (1H, m), 8.04 (1H, dd, J=9.0, 4.72 Hz), 8.00 (1H, s), 7.96-7.88 (1H, m), 7.74 (1H, d, J=8.0 Hz), 7.47 (1H, dd, J=7.2, 4.9 Hz), 7.43-7.34 (1H, m), 7.30 (1H, dd, J=10.3, 9.2 Hz), 5.71 (1H, br s), 1.62 (3H, d, J=7.0 Hz). LCMS (Method K): RT=2.88 min, [M+H]+=400

Provenance & Evidence