[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([OH:8])[CH2:3]1.C(N(CC)C(C)C)(C)C.[Cl:18][C:19]1[C:20]([C:32](Cl)=[O:33])=[N:21][O:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=1>ClCCl>[Cl:18][C:19]1[C:20]([C:32]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][C@H:4]([OH:8])[CH2:3]2)=[O:33])=[N:21][O:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=1A suspension of (1S,3R)-3-aminocyclohexanol (46 mg, 0.40 mmol), N,N-diisopropylethylamine (0.21 mL, 1.20 mmol) and dichloromethane (15 mL) under argon was treated with a dichloromethane (15 mL) solution of 4-chloro-5-(3,4-difluorophenyl)-isoxazole-3-carbonyl chloride (112 mg, 0.40 mmol) at room temperature. After stirring for 2 hours the volatiles were removed in vacuo, and the residue was purified initially by silica gel chromatography, eluting with dichloromethane to 4% methanol in dichloromethane followed by RP HPLC (H2O/MeCN/MeOH 48/48/4 [vol./vol.]) to afford the title compound: (86 mg, 0.24 mmol).
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