Triethylamine → N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(3-methyl-5-isothiazolyl)urea

HRID 1348825Notes

Reaction equation

HRID 1348825 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].C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.Cl.[NH2:44][C:45]1[S:49][N:48]=[C:47]([CH3:50])[CH:46]=1>C(Cl)(Cl)Cl.O>[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:35]([NH:44][C:45]1[S:49][N:48]=[C:47]([CH3:50])[CH:46]=1)=[O:41]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)aniline

Product 1

HCID 22637132N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(3-methyl-5-isothiazolyl)ureaYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline (43 mg) was dissolved in chloroform (1.2 ml) and triethylamine (0.2 ml) to prepare a solution. A solution of triphosgene (20 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 5 min. Next, 5-amino-3-methylisothiazole hydrochloride (22 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was concentrated, and the residue was then purified by chromatography (chloroform:acetone=2:1) to give the title compound (13.7 mg, yield 22%).

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was subjected to separatory extraction with chloroform
  3. concentrationThe organic layer was concentrated
  4. customthe residue was then purified by chromatography (chloroform:acetone=2:1)

Sources & evidence

ORD record
ord-bf6cbac3a0f84c99b64b4ef26b865e77
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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