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

HRID 1361670ノート

反応式

HRID 1361670 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
125 °C

実験手順

[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.

後処理

  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

出典と根拠

ORDレコード
ord-843fb07315d2456f8985d3312e9892e2
出典データセット
uspto-grants-2011_02
特許番号
US07880000B2

反応ノート

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