2-Amino-N-(4-sec-butylphenyl)benzamide → HCID 86659825, compound

HRID 1846373Notes

Reaction equation

HRID 1846373 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[F:21][C:22]([F:36])([F:35])[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][C:27]=1[I:34])=[O:24]>CCO>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:1]=[C:32]2[C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:23](=[O:24])[C:22]([F:35])([F:21])[F:36])=[C:27]([I:34])[CH:28]=2)=[CH:8][CH:9]=1)([CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 167700372-Amino-N-(4-sec-butylphenyl)benzamideHCID 587670712,2,2-Trifluoro-N-(4-formyl-2-iodophenyl)acetamide

Product 1

HCID 86659825HCID 86659825, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-amino-N-(4-sec-butylphenyl)benzamide (0.275 g, 1.00 mmol) and anhydrous CuCl2 (0.275 g, 2.00 mmol) were added to a solution of 2,2,2-trifluoro-N-(4-formyl-2-iodophenyl)acetamide in anhydrous EtOH (15 mL) and heated to reflux temperature for 3 hours. After concentrating in vacuo, the residue was dissolved in EtOAc, washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 60% EtOAc in heptane, afforded N-(4-(3-(4-sec-butylphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2-iodophenyl)-2,2,2-trifluoroacetamide (0.390 g, 66%).

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 3 hours
  3. concentrationAfter concentrating in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 10% to 60% EtOAc in heptane

Sources & evidence

ORD record
ord-0dfdd8b358f44204afd113b6c4d15252
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

Loading…