Hydrochloric Acid → HCID 57345649, compound

Participants

Reaction Steps

Bromo-compound 29 (123 mg, 0.27 mmol) was stirred in CH2Cl2 (10 mL), 40% aqueous HNMe2 (3 mL) and H2O (7.5 mL) at rt for 20 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with H2O (1×10 mL), 10% aqueous NaOH (1×10 mL), and saturated brine (1×10 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a cream solid which was dissolved in acetone and treated with 2 M hydrochloric acid in diethyl ether. A white precipitate was obtained and isolated by filtration to give 24 (44 mg, 36%) as a cream powder. 1H NMR (DMSO-d6, 400 MHz) δ 1.31 (s, 9H, (CH3)3), 1.64 (m, 4H, CH2)2), 2.36 (t, 2H, J=6.7 Hz, COCH2), 2.75 (s, 6H, NH(CH3)2), 3.05 (m, 2H, CH2Br), 7.53 (m, 6H, ArH), 7.98 (d, 2H, J=8.6 Hz, ArH), 9.63 (s(br), 1H, NH), 9.98 (s, 1H, NH), 10.82 (s, 1H, NH), 10.93 (s, 1H, NH).

Provenance & Evidence