Dimethylacetamide → 6-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methylpyrazin-2-yl)quinazoline-4-amine

HRID 81645

반응식

HRID 81645 반응식
[Cl:1][C:2]1[C:3](F)=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:7]=1.CC(C)([O-])C.[K+].CN(C)C(=O)C.[CH3:30][C:31]1[N:32]=[CH:33][C:34]([NH:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([OH:48])[CH:46]=3)[N:41]=[CH:40][N:39]=2)=[N:35][CH:36]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:48][C:45]2[CH:46]=[C:47]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][N:39]=[C:38]3[NH:37][C:34]2[CH:33]=[N:32][C:31]([CH3:30])=[CH:36][N:35]=2)=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:7]=1

참가 물질

6

반응물 4

HCID 31374DimethylacetamideHCID 23665647Potassium tert-butoxideHCID 684276023-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridineHCID 1356182224-((5-Methylpyrazin-2-yl)amino)quinazolin-6-ol

생성물 1

HCID 684277516-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methylpyrazin-2-yl)quinazoline-4-amine수율 53%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

3-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine (460 mg, 1.74 mmol) and potassium tert-butoxide (160 mg, 1.4 mmol) were added to an N,N-dimethylacetamide suspension (0.9 ml) of 4-[(5-methylpyrazin-2-yl)amino]quinazolin-6-ol (180 mg, 0.71 mmol), and reacted under a nitrogen atmosphere at 200° C. for 30 minutes, using microwaves. The reaction solution was cooled to room temperature, then diluted with chloroform. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4) and amine-type silica gel column chromatography (hexane:ethyl acetate=50:50) to obtain 6-{[3-chloro-5-(2,2-diethoxyethoxy)pyridin-2-yl]oxy}-N-(5-methylpyrazin-2-yl)quinazoline-4-amine (187 mg, yield: 53%) as a pale yellow solid.

후처리

  1. customreacted under a nitrogen atmosphere at 200° C. for 30 minutes
  2. washThe organic layer was washed with water and saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4) and amine-type silica gel column chromatography (hexane:ethyl acetate=50:50)

출처 및 근거

ORD 기록
ord-bc572eaa97814650b905e0c3710872ab
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846700B2

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