A mixture of 4-{(1S)-1-[(7-bromo-5-methyl-1-benzothien-3-yl)(4-chlorophenyl)methyl]butyl}benzoic acid (EXAMPLE 3, Step A, 20.0 mg, 0.038 mmol), 1-(2H-tetrazol-5-yl)methanamine (10.9 mg, 0.110 mmol), EDC (22.0 mg, 0.110 mmol), HOBt (17.0 mg, 0.110 mmol) and DIEA (0.050 mL, 0.29 mmol) in DMF (1 mL) was heated at 65° C. for 12 hours. The mixture was allowed to cool to RT, diluted with acetonitrile, then purified by preparative reverse-phase HPLC eluting with 38-100% acetonitrile/water+0.1% TFA. Following lyophilization, this afforded the title compound as a white solid. 1H NMR (500 MHz, d6-DMSO) δ 9.04 (br, 1H); 7.96 (s, 1H); 7.84 (s, 1H); 7.67 (d, J=8 Hz, 2H); 7.64 (d, J=8 Hz, 2H); 7.52 (d, J=8 Hz, 2H); 7.39 (d, J=8.5 Hz, 2H); 7.35 (br, 1H); 4.84 (d, J=11.5 Hz, 1H); 4.67 (d, J=5.5 Hz, 2H); 3.74 (t, J=12 Hz, 1H); 2.40 (s, 3H); 1.44-1.52 (m, 1H); 1.24-1.32 (m, 1H); 0.91 (q, J=7.5 Hz, 2H); 0.67 (t, J=7 Hz, 3H). LC2: 2.63 min. (M+H)+ 608.
