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1-(3-Hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (268 mg, 0.63 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (10 mL). The mixture was stirred for 1 h then concentrated to dryness. The residue was dissolved in CH2Cl2 (4.0 mL), cooled to 0° C. and treated with i-Pr2NEt (0.36 mL, 2.1 mmol), followed by methanesulfonyl chloride (0.16 mL, 2.1 mmol). The reaction mixture was stirred for 4 h, then diluted with EtOAc (200 mL) and washed with saturated aqueous NaHCO3 (2×25 mL). The washes were extracted with EtOAc (2×25 mL). The combined extracts were dried over Na2SO4 and concentrated. A portion of the crude mesylate (197 mg, ca. 0.41 mmol) was combined with (2-oxo-3-piperidin-4-yl-2,3-dihydro-benzoimidazol-1-yl)-acetonitrile (321 mg, 1.25 mmol) in CH2Cl2 (2.0 mL) and DMF (0.5 mL). The resulting mixture was treated with i-Pr2NEt (0.22 mL, 1.3 mmol) and stirred for 60 h. The reaction mixture was partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (75 mL). The EtOAc layer was washed with H2O (2×75 mL), and brine (75 mL). The combined washes were extracted with EtOAc (3×50 mL). The combined extracts were dried over Na2SO4 and concentrated. Purification of the residue by preparative TLC (silica, 1% MeOH/CH2Cl2 then 25% acetone/CH2Cl2) gave 37 mg (14%) of the title compound. HPLC (reverse phase conditions), tR=2.94 min. MS (electrospray): m/z calculated for C31H35F3N7O3S [M++H] 642.25, found 642.25. 1H NMR (CDCl3, 400 MHz): 7.73 and 7.76 (A and B of AA′BB′ Jab=8.2 Hz, 4H), 7.26-7.05 (m, 4H), 4.81 (s, 2H), 4.56 (s, 2H), 4.26 (m, 1H), 4.15 (t, J=6.8 Hz, 2H), 3.70 (t, J=5.8 Hz, 2H), 3.03 (brd, J=11.1 Hz, 2H), 2.95 (t, J=5.7 Hz, 2H), 2.91 (s, 3H), 2.43 (m, 4H), 2.12 (m, 4H), 1.82 (br d, J=9.9 Hz, 2H).

1. concentrationthen concentrated to dryness
2. dissolutionThe residue was dissolved in CH2Cl2 (4.0 mL)
3. stirringThe reaction mixture was stirred for 4 h
4. washwashed with saturated aqueous NaHCO3 (2×25 mL)
5. extractionThe washes were extracted with EtOAc (2×25 mL)
6. dry with materialThe combined extracts were dried over Na2SO4
7. concentrationconcentrated
8. stirringstirred for 60 h
9. customThe reaction mixture was partitioned between EtOAc (150 mL) and saturated aqueous NaHCO3 (75 mL)
10. washThe EtOAc layer was washed with H2O (2×75 mL), and brine (75 mL)
11. extractionThe combined washes were extracted with EtOAc (3×50 mL)
12. dry with materialThe combined extracts were dried over Na2SO4
13. concentrationconcentrated
14. customPurification of the residue by preparative TLC (silica, 1% MeOH/CH2Cl2