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

HRID 2296717노트

반응식

HRID 2296717 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 NH4Cl 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+).

후처리

  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 NH4Cl 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

출처 및 근거

ORD 기록
ord-d19ba1c0510042e9a3ec06fb226ec6d0
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489328B2

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