Pyridine → 3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-1-methyl-pyrazole

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Triphenylphosphine (1.190 g, 4.54 mmol) was dissolved in methylene chloride (40 mL) and cooled to 0° C. To this solution was added N-bromosuccinimide (914 mg, 5.14 mmol) and was stirred at 0° C. until it was completely dissolved and became light purple in color. The 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in PCT WO 2004/052869 A1, Example 1, 1.00 g, 3.02 mmol) was then added and it was stirred at 0° C. for 20 min and then warmed to 25° C. and stirred for 30 min. After such time, 1-methyl-1H-pyrazol-3-ylamine (441 mg, 4.54 mmol) and pyridine (740 μL, 4.53 mmol) were added and it was stirred at 25° C. for 16 h. The reaction was then diluted with water (30 mL) and then extracted with methylene chloride (3×15 mL). The organic layers were then combined and dried over magnesium sulfate, filtered and concentrated in vacuo. Flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes) followed by reverse phase preparative HPLC purification (Column: Thomson C18 ODSA, 5 micron, 50×21.2 mm ID; 30% acetonitrile/water to 100% acetonitrile/water; 30 mL/min flow rate for 15 min run) afforded 3-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-1-methyl-pyrazole (590 mg, 48%) as a white solid: ESI-LRMS m/e calcd for C19H24ClN3O3S [M+] 409.1. found 410.1 [M+H+]; 1H NMR (400 MHz, CDCl3) δ ppm 0.96-1.18 (m, 2H, CH2), 1.35-1.86 (m, 8H, 4×CH2), 2.10-2.21 (m, 1H, CH), 3.24 (s, 3H, SO2CH3), 3.57 (t, J=7.6 Hz, 1H, CH), 3.73 (s, 3H, NCH3), 6.59 (d, J=2.3 Hz, 1H, Ar), 7.21 (d, J=2.3 Hz, 1H, Ar), 7.38 (dd, Jo=8.2, Jm=1.7 Hz, 1H, Ar), 7.50 (d, Jm=1.7 Hz, 1H, Ar), 7.96 (d, Jo=8.2 Hz, 1H, Ar), 8.82 (s, 1H, NH).

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