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

HRID 405175
Notes
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Reaction equation

HRID 405175 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[C:25]1[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[N:29][CH:30]=1)=O.[Cl:41][C:42]1[CH:47]=[C:46]([Cl:48])[CH:45]=[CH:44][C:43]=1[C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=1.CC(O)=O>CCOC(C)=O.ClCCCl>[Cl:41][C:42]1[CH:47]=[C:46]([Cl:48])[CH:45]=[CH:44][C:43]=1[C:49]1[CH:54]=[CH:53][C:52]([NH:55][CH2:15][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=2[C:25]2[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[N:29][CH:30]=2)=[CH:51][CH:50]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 99647252',4'-Dichloro-[1,1'-biphenyl]-4-amineHCID 86674255Ethyl 3-(5-(2-formyl-4-methoxyphenyl)picolinamido)propanoate

Product 1

HCID 71060006Ethyl 3-(5-(2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-4-methoxyphenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (89 mg, 0.42 mmol) was added to a DCE solution (1 mL) of ethyl 3-(5-(2-formyl-4-methoxyphenyl)picolinamido)propanoate (100 mg, 0.28 mmol), 2′,4′-dichloro-[1,1′-biphenyl]-4-amine (100 mg, 0.42 mmol), and AcOH (0.02 mL, 0.28 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), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-4840c3ec70e840e5a22a4f0ea735a746
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748624B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes