Acetic Acid → HCID 178451896, compound

HRID 923414Notes

Reaction equation

HRID 923414 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.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[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

7

Reactant 4

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

Product 1

HCID 178451896HCID 178451896, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Example 99A (0.50 g, 1.59 mmol), 4-fluoroaniline (0.15 g, 1.59 mmol), and acetic acid (0.09 mL, 1.59 mmol) were combined at ambient temperature in methanol (15 mL) and treated with sodium cyanoborohydride (0.10 g, 1.59 mmol) and stirred 17 hours. The mixture was poured into water, extracted into ethyl acetate, dried over sodium sulfate, filtered, and concentrated to give 0.65 g (100%) of the title compound.

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6943c67617648e5bda95cff354748e0
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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