[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]([C:25]([F:28])([F:27])[F:26])=[CH:19][C:18]=1[C:29]1[CH:30]=[CH:31][C:32]([C:35]([NH:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:36])=[N:33][CH:34]=1)=O.[Cl:45][C:46]1[CH:51]=[C:50]([NH2:52])[CH:49]=[CH:48][C:47]=1[C:53]1[CH:58]=[CH:57][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:55][CH:54]=1.CC(O)=O>C(Cl)Cl.ClCCCl>[Cl:45][C:46]1[CH:51]=[C:50]([NH:52][CH2:15][C:17]2[C:22]([O:23][CH3:24])=[CH:21][C:20]([C:25]([F:28])([F:27])[F:26])=[CH:19][C:18]=2[C:29]2[CH:30]=[CH:31][C:32]([C:35]([NH:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:36])=[N:33][CH:34]=2)[CH:49]=[CH:48][C:47]=1[C:53]1[CH:58]=[CH:57][C:56]([C:59]([F:60])([F:61])[F:62])=[CH:55][CH:54]=1Solid NaBH(OAc)3 (74 mg, 0.35 mmol) was added to a DCE solution (1 mL) of ethyl 3-(5-(2-formyl-3-methoxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate (98 mg, 0.23 mmol), 2-chloro-4′-(trifluoromethyl)-[1,1-biphenyl]-4-amine (63 mg, 0.23 mmol) and HOAc (0.01 mL, 0.23 mmol) the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with DCM and washed with saturated aqueous NaHCO3 and water. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.
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