Diisopropylethylamine → HCID 11755651, compound

Participants

Reaction Steps

To a solution INTERMEDIATE 9 (0.120 mg, 0.25 mmol)) in 2 ml of DMF was added HATU (0.132 mg, 0.35 mmol) and diisopropylethylamine (173 μL, 0.99 mmol). The reaction was stirred for 30 minutes, after which was added (250 μL, 0.50 mmol) of 2 N HNCH3 in MeOH and the stirring continued over night. The reaction was concentrated and partitioned between a saturated solution of NaHCO3 and ethyl acetate. The organic layer was separated and the aqueous layer extracted 5 times with ethyl acetate. The organic layers were dried (MgSO4), filtered and concentrated to yield COMPOUND 3. 1H NMR (400 NM, CD3OD): δ 1.07 (m, 3H), 1.21 (m, 3H), 2.32 (m, 2H), 2.90 (s, 3H), 3.02 (m, 2H), 3.24 (m, 4H), 3.40 (m, 2H), 3.50 (m, 2H), 4.34 (s, 2H), 4.55 (s, 1H), 7.33 (d, J=8.2 Hz, 2 H), 7.41 (m, 1H), 7.48 (m, 5H), 7.56 (d, J=8.2 Hz, 2H), 7.63 (m, 2H), 7.93 (m, 1H)

Provenance & Evidence