Dichloromethane → HCID 178491831, compound

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Reaction Steps

A mixture of trans-4-(4-{3-[(1S)-1-(2-chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylic acid (9.00 mg, 0.0176 mmol), dimethylamine hydrochloride (14.4 mg, 0.176 mmol), TBTU (8.48 mg, 0.0264 mmol), DIPEA (0.0153 mL, 0.0881 mmol) and DCM (3 mL, 50 mmol) was stirred at rt for 1 min. The solution was concentrated in vacuo, redissolved in MeOH (1 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.65-1.77 (m, 2H), 1.80 (d, J=7.3 Hz, 3H), 1.89-1.97 (m, 2H), 1.98-2.08 (m, 4H), 2.23 (s, 3H), 2.81 (m, J=11.8, 11.8, 3.4, 3.3 Hz, 1H), 2.95 (s, 3H), 3.16 (s, 3H), 3.65 (br. s., 3H), 4.16-4.30 (m, 1H), 5.06-5.15 (m, 1H), 6.89 (dd, J=9.0, 4.4 Hz, 1H), 7.08 (t, J=8.8 Hz, 1H), 7.34 (d, J=1.3 Hz, 1H), 7.40 (s, 1H), 7.48 (s, 1H), 8.11 (s, 1H). MS (ES+): tri/z=538.24/540.24 (100/50) [MH+]. HPLC: tR=1.45 min (polar—3 min, UPLC-ACQUITY).

Provenance & Evidence