Water → HCID 178484210, compound

Participants

Reaction Steps

A solution of phenyl-methyl(2-(7-(thiophene-2-carboximidamido)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)ethyl)carbamate (200 mg, 0.45 mmol) in 12 mL ethanol was treated with NaOH (178 mg, 4.46 mmol) followed by H2O (5 mL). The mixture was then heated at reflux for 6 hours. A TLC analysis indicated that starting material is present. At this moment, NaOH (90 mg) was added and heating was continued for 1 hour. The solution was concentrated to about 5 mL and partitioned between CH2Cl2 (100 mL) and brine (20 mL). After extraction, the organic layer was separated and the aqueous layer was extracted once more with CH2Cl2 (50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to give a yellow oil. This residue was subjected to flash chromatography on silica gel using 2.5-10% 2M NH3 in MeOH/CH2Cl2 to give a yellow solid (60 mg, 40.5%). 1H-NMR (DMSO-d6) δ 7.70 (d, J=3.3 Hz, 1H), 7.57 (d, J=4.8 Hz, 1H), 7.09-7.06 (m, 1H), 6.91-6.88 (m, 1H), 6.64-6.62 (m, 2H), 6.33-6.31 (m, 2H), 3.14 (t, J=6.3 Hz, 2H), 2.85-2.70 (m, 2H), 2.77-2.61 (m, 4H), 2.31 (s, 3H), 1.67-1.62 (m, 2H), 1.50-1.46 (m, 2H). MS (EI): 329.2 (M+1). ESI-HRMS calculated for C18H25N4S (MH+): 329.1794, Observed: 329.1802.

Provenance & Evidence