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

HRID 405253Notes

Reaction equation

HRID 405253 reaction equation
[CH:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])=[N:18][CH:19]=1)=O.[Cl:30][C:31]1[CH:36]=[C:35]([NH2:37])[CH:34]=[CH:33][C:32]=1[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=1.CC(O)=O.[BH3-]C#N.[Na+].[NH4+].[Cl-]>CCO>[Cl:30][C:31]1[CH:36]=[C:35]([NH:37][CH2:1][C:3]2[C:8]([CH3:9])=[CH:7][C:6]([C:10]([F:12])([F:13])[F:11])=[CH:5][C:4]=2[C:14]2[CH:15]=[CH:16][C:17]([C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])=[N:18][CH:19]=2)[CH:34]=[CH:33][C:32]=1[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 688342842-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amineHCID 86674283HCID 86674283, compound

Product 1

HCID 86674284Ethyl 3-(5-(2-(((2-chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (37 mg, 0.09 mmol), 2-chloro-4′-(trifluoromethyl)-[1,1-biphenyl]-4-amine (39 mg, 0.14 mmol) and HOAc (5 μL, 0.09 mmol) were dissolved in EtOH (2 mL) and the resulting mixture was heated to 80° C. After 5 h the resulting mixture was cooled to room temperature, solid NaCNBH3 (28 mg, 0.45 mmol) was added and the resulting mixture was stirred at room temperature. After 2 h saturated aqueous NH4Cl was added and the aqueous phase was extracted with EtOAc. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. temperatureAfter 5 h the resulting mixture was cooled to room temperature
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-28a5570787624e5a932a57911170a02c
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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