Triethylamine → HCID 91826344, compound

Participants

Reaction Steps

A mixture of 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 27) (150 mg, 0.407 mmol), N-methyl-1H-imidazole-1-carboxamide [Duspara, Petar A.; Islam, Md. Sadequl; Lough, Alan J.; Batey, Robert A. Journal of Organic Chemistry (2012), 77(22), 10362-10368] (50.9 mg, 0.407 mmol) and triethylamine (0.057 mL, 0.407 mmol) in CH2Cl2 (4 mL) was stirred for 16 h at rt. N-methyl-1H-imidazole-1-carboxamide (50 mg) was added. The reaction mixture was stirred for 3 days at rt, diluted with CH2Cl2/water and extracted twice with CH2Cl2. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography (1% ammonia/5% MeOH/DCM), subsequent preparative achiral SFC (column: Reprosil 70 NH2, 250×30 mm, 5 μm, Dr Maisch; eluent: MeOH/scCO2; gradient: 1 min 21% MeOH, 21-26% MeOH in 6 min, 26-50% MeOH, in 1 min, 1.5 min 50% MeOH; flow: 100 mL/min) and trituration of the resulting products in diethyl ether to afford 57 mg of 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-N,3-dimethyl-6-oxo-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxamide (Example 144) and 26 mg of the title compound. tR: 0.84 min (LC-MS 2); ESI-MS: 426.1 [M+H]+ (LC-MS 2); Rf=0.24 (NH3 1%/CH2Cl2/MeOH 5%); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.92 (s, 3H) 1.98 (s, 3H) 2.83 (d, J=4.30 Hz, 3H) 3.35 (s, 3H) 6.17 (s, 1H) 7.26-7.45 (m, 5H) 7.74 (br. s., 1H) 8.53 (d, J=4.30 Hz, 1H).

Provenance & Evidence