Hydrochloric Acid → HCID 11522376, compound

Participants

Reaction Conditions

Reaction Steps

Borane-THF complex in THF (1 M, 2 mL, 2 mmol) was added to a solution of Example 6B in dry THF (6 mL) at r.t. The reaction stirred at reflux for 1 h, and was then cooled to 0° C. Concentrated HCl (0.8 mL) was added slowly, and the reaction was stirred at 60° C. for 1 h. The solution was cooled to 0° C., made basic with ammonium hydroxide, and extracted (3×) with EtOAc. Organics were dried (MgSO4) and concentrated in vacuo. Purification by Prep-HPLC gave 88 mg (51%) white solid as the HCl salt. 1H NMR (400 MHz, MeOD-d4): δ 9.59 (s, 1H), 8.04 (d, 1H, J=8.4 Hz), 7.71 (d, 1H, J=2.0 Hz), 7.50-7.59 (m, 3H), 4.51 (qAB, 2H, J=142.4, 15.2 Hz), 4.45 (s, 3H). MS (ES) [m+H] calc'd for C15H13N3Cl2, 306, 308; found 306, 308.

Provenance & Evidence