Sodium triacetoxyborohydride → Ethyl 3-(5-(5-chloro-2-(((3',4'-difluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

HRID 405218Notes

Reaction equation

HRID 405218 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:38]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[F:40][C:41]1[CH:42]=[C:43]([C:48]2[CH:53]=[CH:52][C:51]([NH2:54])=[CH:50][CH:49]=2)[CH:44]=[CH:45][C:46]=1[F:47]>CC(O)=O.C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:38][NH:54][C:51]2[CH:50]=[CH:49][C:48]([C:43]3[CH:44]=[CH:45][C:46]([F:47])=[C:41]([F:40])[CH:42]=3)=[CH:53][CH:52]=2)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 610262874-(3,4-Difluorophenyl)anilineHCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Product 1

HCID 71059933Ethyl 3-(5-(5-chloro-2-(((3',4'-difluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Solid NaBH(OAc)3 (116 mg, 0.55 mmol) was added to a DCM solution (1 mL) of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (95 mg, 0.27 mmol), 3′,4′-difluoro-[1,1′-biphenyl]-4-amine (73 mg, 0.36 mmol), and 1 drop of AcOH and the resulting mixture was stirred at room temperature. After 3 h the resulting mixture diluted with DCM and saturated aqueous NaHCO3 and the layers were separated. The organic phase was washed with brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-c9ed4ab643ee4801b318f8a051da30ff
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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