Ammonium Chloride → HCID 44199824, compound

Participants

Reaction Steps

To a solution of 1-(3-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenylamino)-1,2,4-oxadiazol-5-yl)cyclopropanecarboxylate 23 (100 mg, 0.22 mmol) in MeOH (10 mL), three batches of NaBH4 (66.5 mg, 1.76 mmol) were added during a period of 30 min. After the reaction was determined to be completed by LC/MS, ammonium chloride solution was added to quench the reaction. The resulting mixture was extracted with DCM (50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to yield a reside which was purified by preparative HPLC to yield 3-(5-(5-(1-(hydroxymethyl)cyclopropyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-di methyl-1,6-naphthyridin-2(1H)-one (A69). 1H NMR (400 MHz, d6-DMSO) δ 9.07 (s, 1H), 8.03 (s, 1H), 7.91 (s, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.33 (dd, J=2.4, 8.4 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 3.87 (s, 2H), 3.83 (s, 3H), 2.86 (s, 3H), 2.16 (s, 3H), 1.35 (m, 2H), 1.21 (m, 2H). MS m/z 418.2 (M+1).

Provenance & Evidence