2-Methoxyethylamine → HCID 44556155, compound

Participants

Reaction Steps

A solution of 4-(5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzaldehyde (47 mg, 0.14 mmol) and 2-methoxyethylamine (65 μL, 0.70 mmol) and 4 Å molecular sieves in tetrahydrofuran (5 mL) was stirred at 24° C. After 18 h, sodium cyanoborohydride (100 mg, 2 mmol) was added to the reaction mixture. After 1 h, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL). The organic was separated and washed with saturated aqueous sodium chloride solution (10 mL). The collected organic was dried over magnesium sulfate, filtered, and concentrated. Purification by preparative HPLC provided a tan solid (18.6 mg, 34%). LCMS (ESI) m/z: 404. 1H NMR (400 MHz, DMSO-d6), δ: 9.51 (s, 1H), 8.05 (d, J=8.8, 2 H), 7.62 (m, 3H), 7.52 (d, J=8.7, 1H), 7.20 (d, J=8.4, 2H), 7.16-7.10 (m, 3H), 3.87 (s, 3H), 3.62 (s, 2H), 3.39 (t, J=5.7, 2H), 3.23 (s, 3H), 3.17 (d, J=5.2, 2H), 2.63 (t, J=5.7, 2H).

Provenance & Evidence