Water → 5-bromo-6-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 1786298ノート

反応式

HRID 1786298 の反応式
[Br:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11](F)=[CH:10][C:9]=2[F:16])=[C:6]([NH:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])[N:5]2[N:24]=[CH:25][N:26]=[C:4]2[N:3]=1.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][OH:32].[H-].[Na+].O>CS(C)=O>[Br:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:32][CH2:31][CH2:30][CH2:29][N:28]([CH3:33])[CH3:27])=[CH:10][C:9]=2[F:16])=[C:6]([NH:17][C@@H:18]([CH3:23])[C:19]([F:22])([F:20])[F:21])[N:5]2[N:24]=[CH:25][N:26]=[C:4]2[N:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 766463-(Dimethylamino)-1-propanolHCID 161030295-bromo-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

生成物 1

HCID 112609665-bromo-6-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine収率 78.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 5-bromo-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine (44 mg, 0.1 mmol) and 3-dimethylamino-1-propanol (51 m g, 0.5 mmol) in 1 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 20 mg, 0.5 mmol). The mixture is heated at 60° C. for 2 h, and cooled to room temperature. Water is added to quench the reaction, and the product is extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride (x3), dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of ethyl acetate to 30% methyl alcohol in ethyl acetate. Concentration provides 5-bromo-6-{4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine as a light tan solid (41 mg, mp 40-42° C.). MS: m/z 523.1, 525.1 (M+H).

後処理

  1. temperaturecooled to room temperature
  2. customto quench
  3. customthe reaction
  4. extractionthe product is extracted with ethyl acetate
  5. washThe organic layer is washed with saturated sodium chloride (x3)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a residue
  8. customThe residue is chromatographed over silica gel
  9. washeluting with a gradient of ethyl acetate to 30% methyl alcohol in ethyl acetate
  10. concentrationConcentration

出典と根拠

ORDレコード
ord-598882ca8c114ffba921317d4c245de0
出典データセット
uspto-grants-2009_03
特許番号
US07507739B2

反応ノート

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