4-Methylmorpholine → HCID 86618344, compound

Participants

Reaction Conditions

Reaction Steps

Compound 3-1 (150 mg, 0.39 mmol) was dissolved in dry DMF (10 mL), and treated with N-methylmorpholine (162 μL, 1.5 mmol), 1-hydroxybenzotriazole (6.3 mg, 0.047 mmol), and phenylpropylamine (70 μL, 0.49 mmol). The reaction mixture was chilled to 4° C. in an ice bath, treated with HBTU (280 mg, 0.74 mmol), and stirred overnight, allowing it to warm to rt. The reaction mixture was poured into EtOAc (50 mL) and washed with 1 N sodium hydroxide solution (3×), 1 N hydrochloric acid solution (3×), and brine. The organic layer was dried over Na2SO4 and concentrated to give a crude product, which was purified on silica gel (elution with 90% EtOAc in hexane) to give Compound 3 (125 mg, 0.25 mmol, 64%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.37-6.98 (m, 13H), 5.97 (t, J=6 Hz, 1H), 4.56 (s, 2H), 4.09 (t, J=7 Hz, 2H), 3.45 (t, J=7 Hz, 2H), 3.10-2.93 (m, 3H), 2.74-2.61 (m, 4H), 2.27, (t of d, J=8 and 3 Hz, 2H), 2.02-1.83 (m, 6H); MS (ES+) m/z 498.3 (M+1); Anal Calcd. for C31H35N3O3-0.18H2O-0.62 HCl: C, 71.13; H, 6.93; N, 8.03; H2O, 0.62. found C, 71.13; H, 6.90; N, 7.91; KF=0.60.

Provenance & Evidence