Methanol → HCID 69352855, compound

HRID 1375867Notes

Reaction equation

HRID 1375867 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][CH2:40][CH3:41].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:38]([N:37]([CH3:36])[C:28]([NH:4][C:3]1[CH:5]=[CH:6][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:8][C:2]=1[Cl:1])=[O:34])[CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 887MethanolHCID 8068N-MethylbutylamineHCID 94429TriphosgeneHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 69352855HCID 69352855, compoundYield 24%

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, N-methylbutylamine (43 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 26 mg (yield 24%) 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-60c9f48172bc4ad8b03261a05c06583f
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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