Cyclohexanol → HCID 25216188、化合物

HRID 2382768ノート

反応式

HRID 2382768 の反応式
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:11]1[N:16]2[N:17]=[C:18]([NH2:20])[N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH:1]1([O:7][C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 214644135-Chloro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

生成物 1

HCID 25216188HCID 25216188、化合物収率 80.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Cyclohexanol (1.68 mL; 15.84 mmol; 5.0 eq.) was added to a suspension of NaH (152 mg; 3.80 mmol; 1.2 eq.) in THF (6.0 mL) and maintained under inert atmosphere at 0° C. The reaction mixture was brought back to rt and stirred for 1 h before the addition of 5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A4), 534 mg; 3.17 mmol; 1.0 eq.). Reaction mixture was then heated at reflux for 3 h after which time it was quenched by addition of water. It was then extracted with EtOAc, washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (DCM/MeOH, 95:5 to 10:90) gave the title compound as a white solid (590 mg, 80%). HPLC, Rt: 2.18 min. (purity 90.1%). LC/MS, M+(ESI): 233.0.

後処理

  1. customwas brought back to rt
  2. customReaction mixture
  3. temperaturewas then heated
  4. temperatureat reflux for 3 h after which time it
  5. customwas quenched by addition of water
  6. extractionIt was then extracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash chromatography on silica gel (DCM/MeOH, 95:5 to 10:90)

出典と根拠

ORDレコード
ord-c19b3b8b4d064619a9c67c3db3309a1f
出典データセット
uspto-grants-2012_09
特許番号
US08263595B2

反応ノート

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