Hydrazinecarboxaldehyde → (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine

HRID 397666노트

반응식

HRID 397666 반응식
[CH:1]([NH:3][NH2:4])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[C:21](=[NH:25])OCC)(=[O:14])=[O:13])=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.O1CCOCC1>[F:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[C:21]2[N:25]=[CH:1][NH:3][N:4]=2)(=[O:13])=[O:14])=[CH:10][CH:11]=1

참가 물질

5

반응물 2

HCID 12229HydrazinecarboxaldehydeHCID 57097015ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidate

생성물 1

HCID 178527361(2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine수율 32.6%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 312751,4-Dioxane용매

실험 절차

Formylhydrazine (120 mg) was added to a solution of ethyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboximidate (295 mg) [see Preparation 41] in toluene (5 ml) and 1,4-dioxane (5 ml). The reaction mixture was stirred at reflux for 26 hours after which time the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate and washed with water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 0:100 (in 10% increments), by volume, hexane:ethyl acetate to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-2-(1H-1,2,4-triazol-3-yl)piperidine (95 mg) as an off-white foam.

후처리

  1. temperatureat reflux for 26 hours after which time the solvent
  2. customwas removed under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent removed under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0 changing to 0:100 (in 10% increments), by volume, hexane

출처 및 근거

ORD 기록
ord-1c9e22cef2ba480d9c6bc29238cd09e3
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610707B1

반응 노트

불러오는 중…