N'-Hydroxy-4-methylbenzenecarboximidamide → 5-(3-Tert-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-7-yl)-3-(p-tolyl)-1,2,4-oxadiazole

HRID 2047646

반응식

HRID 2047646 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:18]([C:22]1[N:26]2[CH2:27][CH2:28][CH:29]([C:31](OCC)=O)[CH2:30][C:25]2=[N:24][N:23]=1)([CH3:21])([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:18]([C:22]1[N:26]2[CH2:27][CH2:28][CH:29]([C:31]3[O:9][N:8]=[C:6]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=4)[N:7]=3)[CH2:30][C:25]2=[N:24][N:23]=1)([CH3:21])([CH3:19])[CH3:20]

참가 물질

7

반응물 4

HCID 209113N'-Hydroxy-4-methylbenzenecarboximidamideHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 67300535Ethyl 3-t-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate

생성물 1

HCID 673002765-(3-Tert-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-7-yl)-3-(p-tolyl)-1,2,4-oxadiazole수율 49%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Add 4-methylbenzamidoxime (1.44 g, 9.3 mmol) to a 1M solution of potassium tert-butoxide (8.6 mL, 8.6 mmol) diluted with tetrahydrofuran (120 mL). Add ethyl 3-t-butyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-7-carboxylate (2.0 g, 7.2 mmol) and stir overnight at room temperature. Dissolve the reaction in a 1:1 mixture of half saturated aqueous sodium bicarbonate and ethyl acetate. Separate the phases and extract the aqueous phase with ethyl acetate. Wash the combined organic layers with aqueous saturated sodium chloride, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by silica gel flash chromatography eluting with 25-100% ethyl acetate:hexane followed by 5% methanol:ethyl acetate. Recrystallize from dichloromethane and hexane to afford the title compound as a white solid (1.19 g). 1H NMR (CDCl3) δ 1.46 (s, 9H), 2.4 (s, 4H), 2.59 (m, 1H), 3.4 (m, 1H), 3.54-3.69 (m, 2H), 4.11 (m, 1H), 4.38 (m, 1H), 7.22-7.33 (m, 2H), 7.9-7.98 (m, 2H).

후처리

  1. dissolutionDissolve
  2. customthe reaction
  3. customSeparate the phases
  4. extractionextract the aqueous phase with ethyl acetate
  5. washWash the combined organic layers with aqueous saturated sodium chloride
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customPurify the resulting residue by silica gel flash chromatography
  10. washeluting with 25-100% ethyl acetate
  11. customRecrystallize from dichloromethane and hexane

출처 및 근거

ORD 기록
ord-ce5642a54e914473b03af3b7a4d38967
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592590B2

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