Benzoyl chloride → 2-(2,6-Dichlorophenylamino)-1-methyl-7-phenyl-1,8-dihydro-9H-imidazo [4,5-f]quinazoline-9-one

HRID 1760752Notes

Reaction equation

HRID 1760752 reaction equation
N[NH-].[C:3](Cl)(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[NH2:19][C:20]1[CH:38]=[CH:37][C:23]2[N:24]=[C:25]([NH:28][C:29]3[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:36])[N:26]([CH3:27])[C:22]=2[C:21]=1[C:39]([NH2:41])=[O:40]>C1COCC1>[Cl:36][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([Cl:35])[C:29]=1[NH:28][C:25]1[N:26]([CH3:27])[C:22]2=[C:21]3[C:20](=[CH:38][CH:37]=[C:23]2[N:24]=1)[N:19]=[C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH:41][C:39]3=[O:40]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 168365Hydrazide (H3N21-)HCID 113939665-Amino-2-(2,6-dichlorophenylamino)-3-methyl-3H-benzoimidazole-4-carboxylic acid amide

Product 1

HCID 1354401472-(2,6-Dichlorophenylamino)-1-methyl-7-phenyl-1,8-dihydro-9H-imidazo [4,5-f]quinazoline-9-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above amino amide (50 mg, 0.15 mmol) was added to a solution of benzoyl chloride (32 mg, 0.23 mmol) in THF (1 mL). Triethylamine (0.03 mL, 0.23 mmol) was added and the mixture stirred for 1 h. TLC showed conversion to the benzamide. The solvent was evaporated and the residue dissolved in MeOH (1 mL). Sodium methoxide in MeOH (25%, 0.2 mL) was added and the solution heated to reflux for 45 min. The cooled mixture was partitioned between 1M NH4C1 and CH2Cl2. The residue from the organic layer was stirred and refluxed with MeOH (2 mL) for 1 h, cooled, filtered and washed with MeOH to yield the title compound, 7 (52 mg, 79%) Mp>300° C. MS (ES+) 436, 438 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in MeOH (1 mL)
  3. additionSodium methoxide in MeOH (25%, 0.2 mL) was added
  4. temperaturethe solution heated
  5. temperatureto reflux for 45 min
  6. customThe cooled mixture was partitioned between 1M NH4C1 and CH2Cl2
  7. stirringThe residue from the organic layer was stirred
  8. temperaturerefluxed with MeOH (2 mL) for 1 h
  9. temperaturecooled
  10. filtrationfiltered
  11. washwashed with MeOH

Sources & evidence

ORD record
ord-a0af2c34208d4204adf5d3c4a5b798df
Source dataset
uspto-grants-2005_01
Patent number
US06844435B2

Reaction notes

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