[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[CH:9]=1)[NH2:6])[CH3:2].N1C(C)=CC=CC=1C.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>O1CCCC1.C(OCC)(=O)C.Cl>[C:28]1([O:27][C:25](=[O:26])[NH:6][C:5]2[CH:7]=[C:8]([C:10]3[N:14]([CH3:15])[N:13]=[N:12][N:11]=3)[CH:9]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1A solution of 3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)aniline (3.83 g, 19 mmol) in tetrahydrofuran was treated with 2,6-lutidine (2.17 mL, 19 mmol) and cooled to 0° C. A solution of phenyl chloroformate (2.36 mL, 19 mmol) in tetrahydrofuran was added dropwise. The mixture was stirred for 1 hour, then was diluted with ethyl acetate and 0.1 N aqueous hydrochloric acid. The separated organic phase was washed twice with 0.1 N aqueous hydrochloric acid, then with saturated aqueous sodium chloride. The solution was dried over magnesium sulfate and concentrated under vacuum to provide a tan solid (6.00 g, quantitative). 1H NMR (300 MHz, CDCl3) δ7.86 (s, 1H), 7.5-7.3 (m, 5H), 7.3-7.1 (m, 3H), 4.17 (s, 3H), 2.71 (q, J=7 Hz, 2H), 1.27 (t, J=7 Hz, 3H).
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