Cyclohexanol → HCID 25216188, 화합물

HRID 2382768노트

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HRID 2382768 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 25216188HCID 25216188, 화합물수율 80.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c19b3b8b4d064619a9c67c3db3309a1f
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263595B2

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