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

HRID 405246Notes

Reaction equation

HRID 405246 reaction equation
[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]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 688342842-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amineHCID 86674280Ethyl 3-(5-(2-formyl-3-methoxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 86674281Ethyl 3-(5-(2-(((2-chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)-3-methoxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Solid 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.

Workup

  1. washwashed with saturated aqueous NaHCO3 and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-86a35a02d84c41ed9dae88d893b183b7
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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