Methanol → HCID 22667089, compound

HRID 1375864Notes

Reaction equation

HRID 1375864 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.[CH3:36][NH:37][CH2:38][CH2:39][CH3:40].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:37]([CH3:36])[CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 887MethanolHCID 12315N-MethylpropylamineHCID 94429TriphosgeneHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 22667089HCID 22667089, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline 56 mg) was dissolved in chloroform (4 ml) and triethylamine (0.3 ml), and a solution of triphosgene (50 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, N-methylpropylamine (26 μl) was added to the reaction solution, and the mixture was stirred at room temperature for additional one hr. 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 42 mg (yield 58%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for additional one hr
  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-5f6741e68b934ff0abc3fcd4f1a6f37c
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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