Trifluoroacetic acid → HCID 75203705, compound

Participants

Reaction Steps

40 mg (0.138 mmol) of (3S)-1-(8-methylpyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-amine dihydrochloride and 31 mg (0.138 mmol) of 1-(4-chlorophenyl)pyrazole-3-carboxylic acid were dissolved in 0.5 mL of NMP. To this mixture were added 79 mg (0.207 mmol) of HATU and 0.120 mL (0.690 mmol) of N,N-diisopropylethylamine. The mixture was stirred at rt for 1 hour, then diluted with 3 mL of DMSO and injected directly onto a reverse-phase semi-preparative HPLC system (5-60% acetonitrile/water, 0.1% TFA). Pure fractions were concentrated in vacuo, dissolved in 1 mL of methanol and passed through a bicarbonate resin cartridge (PL-HCO3 MP SPE 500 mg/6 mL). To the resulting solution 15 μL of concentrated hydrochloric acid was added and the volatiles were removed in vacuo to give 49 mg of the desired product as an HCl salt (78% yield). 1H NMR (400 MHz, DMSO) δ 11.38 (s, 1 H), 8.78 (d, J=7.0 Hz, 1 H), 8.59 (d, J=3.0 Hz, 1 H), 7.95 (d, J=7.0, 2 H), 7.81 (m, 2 H), 7.61 (d, J=8.8 Hz, 2 H), 6.92 (s, 1 H), 6.85 (d, J=5.5 Hz, 1 H), 6.76 (d, J=2.2 Hz, 1 H), 4.70-4.65 (m, 1 H), 4.18-3.80 (m, 4 H), 2.48 (s, 3 H), 2.38-2.18 (m, 2 H); MS: (ES) m/z calculated for C22H21ClN6O [M+H]+ 421.2, found 421.

Provenance & Evidence