Trifluoroacetic acid → HCID 86729754, compound

HRID 2272595Notes

Reaction equation

HRID 2272595 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][CH2:10][CH:11]([CH3:21])[CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:8])=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>>[NH2:13][CH2:12][CH:11]([CH3:21])[CH2:10][NH:9][C:7](=[O:8])[C:6]1[CH:22]=[CH:23][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729753HCID 86729753, compound

Product 1

HCID 86729754HCID 86729754, compoundYield 93%

Procedure

A solution of the compound obtained in Step 1 (311 mg, 0.98 mmol) in TFA (1 mL, 12.98 mmol) was stirred at room temperature for 15 min, and concentrated under reduced pressure. To the residue were added ethyl acetate and 1N aqueous sodium hydroxide solution, and the organic layer was separated. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure to give N-(3-amino-2-methylpropyl)-4-cyanobenzamide (198 mg, 0.911 mmol, 93%) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue were added ethyl acetate and 1N aqueous sodium hydroxide solution
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ea71da72c2ae484894e00a9812b9d64f
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

Loading…