Dichloromethane → HCID 21309671, compound

Participants

Reaction Conditions

Reaction Steps

A 1.3 g sample of the compound from step 59a above was dissolved in 6 mL of methylene chloride, the solution was cooled to 0° C., and 4 mL of TFA was added. The reaction mixture was stirred at 0° C. for 3 hours, then poured into a satd solution of K2CO3. The organic layer was separated, the aqueous layer extracted with additional methylene chloride, the organics combined, and the solvent removed. The residue was dissolved in ethanol, the solution was cooled to 0° C., and excess NaCNBH3 was added. Two mL of HCHO were added, the pH was adjusted with acetic acid, using bromocresol as an indicator, and the reaction mixture was stirred for 16 hours. The reaction was quenched by pouring it into satd K2CO3 solution. The mixture was extracted with methylene chloride, the extract was dried over MgSO4, and the solvent was removed. The residual oil was purified by chromatography on silica gel, eluting with 100:1 to 95:5 CHCl3 :methanol containing 0.5% NH4OH. This compound was treated with HCl in ether according to Example 14c to afford 362 mg of the title compound. MS (DCI/NH3) m/e: 193 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.33 (d, J=2.2 Hz, 1H), 7.92 (dd, J=2.6, 8.8 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 4.87-4.77 (m, 1H), 4.57-4.44 (m, 2H), 4.33-4.23 (m, 1H), 4.01 (q, J=9.6 Hz, 1H), 3.00 (s, 3H), 2.73-2.61 (m, 2H), 2.64 (s, 3H). Anal. Calc. for C11H16N2O.2 HCl.0.4 H2O: C, 49.88; H, 6.84; N, 10.56; Found C, 48.25; H, 6.96; N, 10.28.

Provenance & Evidence