Acetic Acid → Ethyl 3-(5-(3-chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405194Notes

Reaction equation

HRID 405194 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[C:17]([CH:42]=O)=[C:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:33])=[N:30][CH:31]=2)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][C:52]=2[CH3:58])=[CH:47][CH:46]=1.CC(O)=O>CCOC(C)=O.C([O-])([O-])=O.[K+].[K+].ClCCCl>[Cl:15][C:16]1[C:17]([CH2:42][NH:57][C:54]2[CH:55]=[CH:56][C:51]([C:48]3[CH:49]=[CH:50][C:45]([Cl:44])=[CH:46][CH:47]=3)=[C:52]([CH3:58])[CH:53]=2)=[C:18]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:33])=[N:30][CH:31]=2)[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydride2×HCID 600391884'-Chloro-2-methyl-[1,1'-biphenyl]-4-amineHCID 86674266Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 71060161Ethyl 3-(5-(3-chloro-2-(((4'-chloro-2-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 11430Potassium CarbonateSolvent

Procedure

Solid NaBH(OAc)3 (2.6 g, 12.1 mmol) was added to a DCE solution (16 mL) of ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (2.6 g, 6.1 mmol) and 4′-chloro-2-methyl-[1,1′-biphenyl]-4-amine (1.6 g, 7.3 mmol), and AcOH (1.4 mL, 1.2 mmol) and the resulting mixture was stirred at room temperature. After 2 h additional NaBH(OAc)3 (2.6 g, 12.1 mmol) was added. After 4 h the resulting mixture was diluted with EtOAc and 2M aqueous K2CO3 and the layers were separated. The aqueous phase was added was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. customthe layers were separated
  2. additionThe aqueous phase was added
  3. extractionwas extracted with EtOAc
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-f48091eecadf41bdbabbc4e8e1f46027
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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