Methanol → HCID 22667174, compound

HRID 1008389Notes

Reaction equation

HRID 1008389 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.Cl.[CH2:36]([NH2:38])[CH3:37].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:27]([NH:38][CH2:36][CH3:37])=[O:33])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11198Ethylamine hydrochlorideHCID 94429TriphosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 1

HCID 22667174HCID 22667174, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.2 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, ethylamine hydrochloride (69 mg) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. Methanol was added to the reaction solution, and the solution was purified by HPLC by development with chloroform/methanol to give 10 mg (yield 16%) of the title compound.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. customthe solution was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-b4881dd44a5443c58b5305659e9d52f9
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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