Acetic Acid → HCID 71060047, compound

HRID 405238Notes

Reaction equation

HRID 405238 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.[Br:40][C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=1.CC(O)=O>C(Cl)Cl.ClCCCl>[Br:40][C:41]1[CH:47]=[CH:46][C:44]([NH:45][CH2:38][C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][C:20]=2[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:43][CH:42]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 78074-BromoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Product 1

HCID 71060047HCID 71060047, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Solid NaBH(OAc)3 (709 mg, 3.3 mmol) was added to a DCE solution (8 mL) of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (603 mg, 1.7 mmol), 4-bromoaniline (287.6 mg, 1.67 mmol) and HOAc (0.10 mL, 1.7 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-14707dd677e749c694f0b5103c4a8622
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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