Dimethylformamide → HCID 131724229, compound

Participants

Reaction Steps

1H-1-Carboxamidine hydrochloride (271 mg,1.85 mmol), and DIPEA (0.5 mL, 3.87 mmol) were added to a vigorously stirring solution of amine 13 (450 mg, 1.42 mmol) in DMF (1.5 ml). The reaction was stirred for 14 hrs then worked up by diluting with Et2O. The viscous oil was repeatedly washed with Et2O, then recrystillized from CH2Cl/MeOH2 giving pure 14 (382 mg, 68%) as a off-white solid: 1H NMR (270 MHz, DMSO-d6) δ8.16(d, J=8.2 Hz, 1H, ArNO2) 8.03(d, J=8.2 Hz ArNO2), 1H, 7.87(t, J=8.2 Hz, 1H ArNO2), 7.66(t, J=8.2 Hz, 1H, ArNO2), 7.45(t, J=5.2 Hz, 1H, RCH2NH), 7.11(s, 2H, Ar—H), 5.80(d, J=4.1 Hz, LH RO—H), 5.14(s, 2H, ArOCH2Ar(NO2)), 4.60 (m, 1H, ArCH(OH)), 3.31 (m, 2H, CH2NH), 2.21(s, 6H, ArCH3) 13C NMR (67.5 MHz, MeOH-d4)δ159.3, 156.3, 148.2, 138.7, 135.1, 135.1, 132.1, 129.9, 129.6, 127.7, 125.8, 73.0, 71.3, 50.0, 16.8;

Provenance & Evidence