Methanol → HCID 22667225, compound

HRID 1008396Notes

Reaction equation

HRID 1008396 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.FC1[CH:43]=[C:42](F)[CH:41]=[CH:40][C:37]=1[CH2:38][NH2:39].CO.C([N:49](CC)CC)C>C(Cl)(Cl)Cl>[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:49][CH2:43][C:42]2[CH:41]=[CH:40][CH:37]=[CH:38][N:39]=2)=[O:33])=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 94429TriphosgeneHCID 27332442,4-DifluorobenzylamineHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 1

HCID 22667225HCID 22667225, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

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, 2,4-difluorobenzylamine (31 μl) was added to the reaction solution, and the mixture was 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 31 mg (yield 43%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-1e4f5e5f40df4e45ab7290e130ab53a9
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

Loading…