Hydrochloric Acid → HCID 58052498, compound

Participants

Reaction Steps

To a solution of 5-[(5-cyclopropyl-3-methylcarbamoyl-2-p-tolyl-furo[2,3-b]pyridin-6-yl)-methanesulfonyl-amino]-pent-2-enoic acid methyl ester (26 mg, 0.051 mmol, 1.0 equiv) in DCM (0.5 mL) was added dimethyl amine (0.10 mL, 2.0 M in THF, 0.2 mmol, 4.0 equiv) and LiClO4 (10.8 mg, 0.1 mmol, 2.0 equiv). The mixture was stirred at room temperature for 24 hours. The reaction mixture was then diluted with THF (0.3 mL), water (0.3 mL), MeOH (0.3 mL) and to the solution was added LiOH (4.9 mg, 0.2 mmol, 5.0 equiv). The mixture was heated at 55° C. for 20 minutes. The solution was neutralized to pH=7 by addition of 1.0 N HCl aq. solution. The mixture was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by reverse phase HPLC with ammonium hydroxide as modifier to give product 6.0 mg. MS (ESI) m/z 543.6 (M+1). Retention time=1.09 min, Method A. 1H NMR (400 MHz, MeOD) d ppm 0.77-0.92 (m, 2H) 1.09-1.20 (m, 2H) 1.61-1.75 (m, 1 H) 2.00-2.11 (m, 1H) 2.37-2.47 (m, 4H) 2.48-2.58 (m, 2H) 2.68 (s, 6H) 2.93 (s, 3 H) 3.17 (s, 3H) 3.51-3.62 (m, 1H) 3.82-3.94 (m, 1H) 3.94-4.04 (m, 1H) 7.35 (d, J=8.03 Hz, 2H) 7.59 (s, 1H) 7.79 (d, J=8.53 Hz, 2H)

Provenance & Evidence