Methanol → HCID 22667219, compound
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][NH:38][CH3:39].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](=[O:34])[N:38]([CH3:39])[CH3:37]Participants
7
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 dimethylamine hydrochloride (250 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 33 mg (yield 53%) of the title compound.
Workup
- temperatureNext, the reaction solution was cooled to −78° C.
- temperatureThe temperature of the mixture was spontaneously raised
- stirringthe mixture was further stirred at room temperature overnight
- customthe mixture was purified by HPLC by development with chloroform/methanol
Sources & evidence
- ORD record
- ord-a689bbb0bd794b1c88306fc696acb63f
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797823B1
Reaction notes
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