N[C@H](C1C=NC=C(Br)C=1)[C@@H](C1C=C(F)C=CC=1F)O.[Cl:20][C:21]1[N:26]=[CH:25][N:24]=[C:23]([C@@H:27]([NH:37]C(=O)OC(C)(C)C)[C@@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[OH:29])[CH:22]=1.O.C(O)(C(F)(F)F)=O>CC#N>[ClH:20].[ClH:20].[NH2:37][C@H:27]([C:23]1[CH:22]=[C:21]([Cl:20])[N:26]=[CH:25][N:24]=1)[C@@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1)[OH:29]Prepared according to the same procedure as (1R,2R)-2-amino-2-(5-bromopyridin-3-yl)-1-(2,5-difluorophenyl)ethanol, starting with tert-butyl(1R,2R)-1-(6-chloropyrimidin-4-yl)-2-(3-fluorophenyl)-2-hydroxyethylcarbamate. Analytical HPLC method: Phenomenex LUNA C18, 50×2 3μ, A=90% H2O/10% CH3CN, B=90% CH3CN/10% H2O, Modifier 0.1% TFA, 0.00 min=0% B, 4.0 min=100% B, 5.0 min=100% B, Flow rate=0.8 mL/min., TR=1.460 min, Mass spec.: 268.1 (MH)+.
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