Acetic Acid → HCID 178451896, compound

HRID 923413Notes

Reaction equation

HRID 923413 reaction equation
[CH:1]([C:3]1[CH:23]=[CH:22][C:6]2[NH:7][C:8]([C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:9][C:5]=2[CH:4]=1)=O.[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.CC(O)=O.C([BH3-])#N.[Na+]>CO>[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][CH2:1][C:3]2[CH:23]=[CH:22][C:6]3[NH:7][C:8]([C@@H:10]4[CH2:14][CH2:13][CH2:12][N:11]4[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[N:9][C:5]=3[CH:4]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 5003444Sodium cyanoborohydrideHCID 178451901HCID 178451901, compound

Product 1

HCID 178451896HCID 178451896, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the product from Example 95A (1.0 g, 3.17 mmol), 4-fluoroaniline (304 μL, 3.17 mmol) and AcOH (150 μL) in MeOH (30 mL) was added sodium cyanoborohydride (199 mg, 3.17 mmol). The mixture was stirred at rt overnight, and was then quenched with aqueous 1N HCl followed by stirring for 5 minutes. A few drops of aqueous NH4OH were added, and the mixture was diluted with EtOAc and washed with saturated aq. NaHCO3, H2O, and brine. The organic layer was dried (MgSO4), filtered and concentrated to afford the title compound (1.3 g, 100%). MS (ESI) m/z 411 (M+H)+.

Workup

  1. customwas then quenched with aqueous 1N HCl
  2. stirringby stirring for 5 minutes
  3. additionA few drops of aqueous NH4OH were added
  4. additionthe mixture was diluted with EtOAc
  5. washwashed with saturated aq. NaHCO3, H2O, and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c28600bdbfee460f91077159b030a9b7
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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