Pyridine → HCID 145857630, compound

Participants

Reaction Steps

A solution of [4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 25: step c) 0.150 g, 0.290 mmol) in dry CH2Cl2 (10 mL) was treated with pyridine (0.026 mL, 0.319 mol) and p-nitrophenyl chloroformate (0.064 g, 0.319 mmol) and stirred 1.7 h. The reaction mixture was treated with ethylene diamine (0.194 mL, 2.90 mmol) and triethylamine (0.485 mL, 3.48 mmol) and stirred at room temperature 16 h. The reaction was diluted with CH2Cl2 and washed with water (3×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the product [(4-{2′-[3-(2-amino-ethyl)-ureido]-6′-methyl-biphenyl-3-sulfonyl}-5-methylsulfanyl-thiophen-2-yl)-imino-methyl]-carbamic acid tert-butyl ester (0.145 g, 82%) as a tan solid. 1H NMR (MeOD): δ 8.195 (s, 1H), 8.057 (d, 1H, J=8.0 Hz), 7.902 (t, 1H, J=1.6 Hz), 7.718 (t, 1H, J=8.0 Hz), 7.554 (d, 1H, J=8.0 Hz), 7.511 (d, 1H, J=8.0 Hz), 7.289 (t, 1H, J=7.6 Hz), 7.119 (d, 1H, J=7.2 Hz), 3.099 (m, 2H), 2.676 (s, 3H), 2.621 (m, 2H), 2.007 (s, 3H), 1.511 (s, 9H). C27H33N5O5S3: 604.16 (M+1) found 603.90.

Provenance & Evidence