Triethylamine → HCID 22637137, compound

HRID 1348853Notes

Reaction equation

HRID 1348853 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.C(N(CC)CC)C.ClC(Cl)(O[C:34](=[O:40])OC(Cl)(Cl)Cl)Cl.Cl.[NH2:43][C:44]1[S:45][C:46]([CH3:50])=[C:47]([CH3:49])[N:48]=1>C(Cl)(Cl)Cl.O>[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:34]([NH:43][C:44]2[S:45][C:46]([CH3:50])=[C:47]([CH3:49])[N:48]=2)=[O:40])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

Product 1

HCID 22637137HCID 22637137, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (40 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, 2-amino-4,5-dimethylthiazole hydrochloride (24 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 (25.8 mg, yield 42%).

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-aef2ae21c4c14047a796e3a6ae7f384f
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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