Benzoyl chloride → HCID 11582406, compound

HRID 1173481Notes

Reaction equation

HRID 1173481 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[CH2:3][CH2:2][NH:1][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:6][C:7]=1[C:13]([F:15])([F:16])[F:14])#[N:10]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86623740HCID 86623740, compound

Product 1

HCID 11582406HCID 11582406, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude 4-[(2-aminoethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.018 mg, 0.058 mmol) in CH2Cl2 (3 mL) was treated with TEA (0.0064 g, 0.063 mmol) and benzoyl chloride (0.0089 mg, 0.063 mmol) and stirred at rt for 1 h. The mixture was partitioned between EtOAc and 0.1N HCl. The organic phase was washed with 0.1N HCl and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5-70% EtOAc/hexanes gradient) and the product crystallized from CH2Cl2/hexanes to give the title compound as a white solid (0.016 g, 66% yield): MS (ES) mlz 416 (M+1).

Workup

  1. customThe mixture was partitioned between EtOAc and 0.1N HCl
  2. washThe organic phase was washed with 0.1N HCl and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-70% EtOAc/hexanes gradient)
  6. customthe product crystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-af594ab29c254051af25ec027acc7572
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

Loading…