Acetic Acid → HCID 71060006, compound

HRID 405175Notes

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

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 99647252',4'-Dichloro-[1,1'-biphenyl]-4-amineHCID 86674255HCID 86674255, compound

Product 1

HCID 71060006HCID 71060006, compound

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
Patent number
US08748624B2

Reaction notes

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