Dimethylamine → HCID 122512301, compound

Participants

Reaction Steps

A mixture of 2-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-propionaldehyde (170 mg; 0.43 mmol; 1 eq.), a 1M solution of dimethyl-amine in THF (2.1 mL; 2.1 mmol; 5 eq.) and sodium triacetoxyborohydride (117 mg; 0.55 mmol; 1.3 eq.) in DCE (10 mL) was stirred at 70° C. for 16 hours. The solution was diluted with DCM, washed with sat. aq. NaHCO3 then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (DCM to 20% MeOH in DCM) followed by hydrochloride formation with a 4M solution of HCl in 1,4-dioxane and crystallization from hot MTBE afforded the title compound (40 mg, 20%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 9.83 (br s, 1H), 7.54-7.45 (m, 1H), 7.41 (ddd, J=7.6, 3.9, 1.7 Hz, 1H), 7.26 (d, J=8.5 Hz, 1H), 7.13 (t, J=7.4 Hz, 1H), 5.04-4.91 (m, 1H), 4.90-4.80 (d, J=7.9 Hz, 2H), 4.71-4.41 (m, 2H), 2.85 (s, 1.5H), 2.82 (s, 1.5H), 2.75 (br s, 6H), 2.63 (s, 1.5H), 2.56 (s, 1.5H), 1.30-1.22 (m, 3H). HPLC (max plot) 98.7%, Rt 2.79 min. UPLC/MS: (MS+) 428.3 ([M+H]+).

Provenance & Evidence