Methanol → HCID 22667185, compound

HRID 1008428Notes

Reaction equation

HRID 1008428 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].ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[CH2:36]([NH:39][CH2:40][CH2:41][CH3:42])[CH2:37][CH3:38].CO>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:28](=[O:34])[N:39]([CH2:40][CH2:41][CH3:42])[CH2:36][CH2:37][CH3:38]

Participants

7

Reactant 4

HCID 887MethanolHCID 8902DipropylamineHCID 94429TriphosgeneHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 22667185HCID 22667185, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (100 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene (90 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 15 min. Next, dipropylamine (62 μl ) was added to the reaction solution, and the mixture was stirred at room temperature for additional 30 min. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol. The solvent was removed by distillation, and the resultant crystal was washed with hexane to give 48 mg (yield 35%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for additional 30 min
  2. customthe mixture was purified by HPLC by development with chloroform/methanol
  3. customThe solvent was removed by distillation
  4. washthe resultant crystal was washed with hexane

Sources & evidence

ORD record
ord-f85b354333b04712bcbb1219897a48d6
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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