Methanol → HCID 9930233, compound

HRID 1375870Notes

Reaction equation

HRID 1375870 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.Cl.[CH3:37][NH2:38].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]([NH:38][CH3:37])=[O:34]

Participants

7

Reactant 4

HCID 887MethanolHCID 94429TriphosgeneHCID 6364545Methylamine hydrochlorideHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 9930233HCID 9930233, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline 50 mg) was dissolved in chloroform (2 ml) and triethylamine (0.5 ml), and a solution of triphosgene (48 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, the reaction solution was cooled to −78° C., and methylamine hydrochloride (130 mg) was added to the cooled reaction solution. The temperature of the mixture was spontaneously raised, and the mixture was further stirred at room temperature overnight. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol to give 41 mg (yield 70%) of the title compound.

Workup

  1. temperatureNext, the reaction solution was cooled to −78° C.
  2. temperatureThe temperature of the mixture was spontaneously raised
  3. stirringthe mixture was further stirred at room temperature overnight
  4. customthe mixture was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-8629a62d3ba8417886205e76e307d6c1
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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