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

HRID 405129Notes

Reaction equation

HRID 405129 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.[Cl:40][C:41]1[CH:46]=[C:45]([NH2:47])[CH:44]=[CH:43][C:42]=1[C:48]1[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=1.CC(O)=O>CCOC(C)=O.ClCCCl>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:38][NH:47][C:45]2[CH:44]=[CH:43][C:42]([C:48]3[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=3)=[C:41]([Cl:40])[CH:46]=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 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 198789103-Chloro-4-(4-chlorophenyl)benzenamineHCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Product 1

HCID 71059870Ethyl 3-(5-(5-chloro-2-(((2,4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (2.7 g, 12.7 mmol) was added to a DCE solution (22 mL) of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate, prepared as in Example 6, (2.3 g, 6.3 mmol), 2,4′-dichloro-[1,1′-biphenyl]-4-amine (1.7 g, 7.0 mmol), and AcOH (1.5 mL, 25.4 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry-packed onto silica gel and purified via column chromatography

Sources & evidence

ORD record
ord-fc5db06525134d90b52b823b8bb948ca
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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