Dimethyl Sulfoxide → 4-methyl-3-((3-(6-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)-N-(3-(trifluoromethyl)phenyl)benzamide

HRID 446318노트

반응식

HRID 446318 반응식
Cl[C:2]1[C:7]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH3:15])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:16][C:17]1[CH:18]=[C:19]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:20]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)=[O:21].C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O>O>[CH3:36][C:35]1[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=2)=[O:21])=[CH:18][C:17]=1[O:16][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:14][CH3:15])[N:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 283918803-hydroxy-4-methyl-N-[3-(trifluoromethyl)phenyl]benzamideHCID 589422526-(2-chloropyridin-3-yl)-N-methylpyrimidin-4-amine

생성물 1

HCID 585880184-methyl-3-((3-(6-(methylamino)-4-pyrimidinyl)-2-pyridinyl)oxy)-N-(3-(trifluoromethyl)phenyl)benzamide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
125 °C

실험 절차

[6-(2-Chloro-pyridin-3-yl)-pyrimidin-4-yl]-methyl-amine (55 mg, 0.25 mmol), 3-hydroxy-4-methyl-N-(3-trifluoromethyl-phenyl)-benzamide (81 mg, 0.27 mmol), Cs2CO3 (162 mg, 0.50 mmol) and DMSO (0.8 mL) were combined. The mixture was heated overnight at 125° C. in a sealed tube. The resulting mixture was cooled to RT, diluted with water and extracted with EtOAc. The aqueous layer was neutralized (pH˜7) with TFA and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to yield the title compound. MS m/z=480 [M+1]+. Calc'd for C25H20F3N5O2: 479.47.

후처리

  1. temperatureThe resulting mixture was cooled to RT
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-419872172b3048eaa39ae572376dbec3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476434B2

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