Methanol → HCID 22667063, compound

HRID 1375868Notes

Reaction equation

HRID 1375868 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:25]([Cl:35])(OC(=O)OC(Cl)(Cl)Cl)Cl.ClC1[CH:44]=[CH:43][C:40]([NH:41][CH3:42])=[CH:39][CH:38]=1.[CH3:45][OH:46]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:45](=[O:46])[N:41]([C:40]1[CH:39]=[CH:38][C:25]([Cl:35])=[CH:44][CH:43]=1)[CH3:42]

Participants

7

Reactant 4

HCID 887MethanolHCID 702724-Chloro-N-methylbenzenamineHCID 94429TriphosgeneHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 22667063HCID 22667063, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline 80 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (72 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 15 min. Next, 4-chloro-N-methylaniline (35 μl) was added to the reaction solution, and the mixture was heated under reflux for additional 30 min. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol, and the solvent was removed by distillation. The resultant crystal was washed with ether to give 83 mg (yield 69%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for additional 30 min
  3. customthe mixture was purified by HPLC by development with chloroform/methanol
  4. customthe solvent was removed by distillation
  5. washThe resultant crystal was washed with ether

Sources & evidence

ORD record
ord-5ec84aebe3db403ebfaf410fb6685623
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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