Ammonium Acetate → 3-Benzyl-7-chloro-2-[2-methyl-1-(2-phenyl-imidazol-1-yl)-propyl]-3H-quinazolin-4-one

HRID 490250Notes

Reaction equation

HRID 490250 reaction equation
[CH2:1]([N:8]1C(=O)C2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:24]([CH2:33][CH:34](OC)OC)[C:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]([O-:42])(=O)[CH3:40].[NH4+:43]>C(O)(=O)C>[CH2:1]([N:8]1[C:39](=[O:42])[C:40]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:20]([N:24]1[CH:33]=[CH:34][N:43]=[C:25]1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 21097051N-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-N-(2,2-dimethoxy-ethyl)-benzamide

Product 1

HCID 98908193-Benzyl-7-chloro-2-[2-methyl-1-(2-phenyl-imidazol-1-yl)-propyl]-3H-quinazolin-4-oneYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propyl]-N-(2,2-dimethoxy-ethyl)-benzamide (288 mg, 0.539 mmol) and ammonium acetate (374 mg, 4.85 mmol) in acetic acid (4.0 mL) was refluxed for 2.0 h. The reaction was concentrated in vacuo and the residue was dissolved in ethyl acetate and washed sequentially with saturated sodium carbonate, water, and brine. The organic layer was dried (Na2SO4), concentrated in vacuo, and recrystallized from ethanol to give the title compound as tan crystals (57.1 mg, 23%). MS(ES+) m/e 469 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed sequentially with saturated sodium carbonate, water, and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1ad5568431fe40ea927d5be975ab59fa
Source dataset
uspto-grants-2009_05
Patent number
US07528137B2

Reaction notes

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