Trifluoroacetic acid → HCID 131736426, compound

Participants

Reaction Steps

A solution of (rac)-tert-butyl ((cis)-3-((3-methyl-8-((R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4-oxo-3,4-dihydroquinazolin-2-yl)amino)cyclohexyl)carbamate (509, see below) (47 mg, 0.093 mmol) and TFA (71.5 pt, 0.928 mmol) in DCM (928 pt) was stirred at RT for 1.5 h when mostly product was observed via LCMS. The reaction mixture was concentrated to give (rac)-2-(((cis)-3-aminocyclohexyl)amino)-3-methyl-8-((R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)quinazolin-4(3H)-one TFA salt (506, 48 mg, 0.092 mmol, 99% yield) as an off-white solid and a 2.6:1 ratio of diastereomers via LCMS and 1.3:1 via 1H NMR. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21-1.33 (m, 1H) 1.33-1.46 (m, 5H) 1.46-1.56 (m, 1H) 1.89 (d, J=12.72 Hz, 1H) 1.98 (d, J=11.74 Hz, 1H) 2.06 (d, J=10.56 Hz, 1H) 2.30-2.39 (m, 1H) 3.05-3.17 (m, 1H) 3.45 (s, 3H) 4.01-4.15 (m, 1H) 4.50-4.61 (m, 1H) 6.93-7.01 (m, 1H) 7.06 (d, J=4.11 Hz, 1H) 7.17 (t, J=7.63 Hz, 1H) 7.62 (s, 0.42H) 7.66 (s, 0.58; H) 7.84 (d, J=7.63 Hz, 1H) 7.88-8.00 (m, 3H) 11.78 (s, 0.42; H) 11.91 (s, 0.58; H). 19F NMR (376 MHz, DMSO-d6) δ ppm −73.81 (s, 3F). MS (ESI, pos. ion) m/z: 407.1 (M+1).

Provenance & Evidence