Sodium hydride → 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine

HRID 1452966ノート

反応式

HRID 1452966 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[NH2:9].[CH:10]([N:13]=[C:14]=[S:15])([CH3:12])[CH3:11].[H-].[Na+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][C:3]2[N:9]=[C:14]([NH:13][CH:10]([CH3:12])[CH3:11])[S:15][C:2]=2[CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 75263Isopropyl IsothiocyanateHCID 5957294,6-Dichloropyridin-3-amine

生成物 1

HCID 575272276-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine収率 61.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4,6-dichloropyridin-3-amine (0.50 g, 3.07 mmol, 1.0 eq.) and isopropyl isothiocyanate (0.33 mL, 3.10 mmol, 1.0 eq.) in DMF under nitrogen at 0° C. was added NaH (60% in mineral oil, 0.194 g, 4.85 mmol, 1.6 eq.). After 10 min., the cold bath was removed, and the reaction mixture was stirred to room temperature for 10 min. It was then heated at 65° C. for 1 hr and cooled to room temperature. At 0° C., aqueous HCl (1 N), water and EtOAc were added, and the reaction mixture was stirred. The layers were separated, and the organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (100:1) as eluent afforded 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine as a white solid (0.43 g, 61% yield).

後処理

  1. customthe cold bath was removed
  2. temperatureIt was then heated at 65° C. for 1 hr
  3. temperaturecooled to room temperature
  4. additionAt 0° C., aqueous HCl (1 N), water and EtOAc were added
  5. stirringthe reaction mixture was stirred
  6. customThe layers were separated
  7. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-57c943ebc1e94228bbaa889767f6d5e3
出典データセット
uspto-grants-2009_01
特許番号
US07473784B2

反応ノート

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