Sodium Bicarbonate → HCID 67300411, compound

HRID 2047647Notes

Reaction equation

HRID 2047647 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:7][CH3:8])[C:3]([NH:5][NH2:6])=O.CO[C:12]1[CH2:17][CH:16]([C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:19]=2)[CH2:15][CH2:14][N:13]=1.C(=O)(O)[O-].[Na+]>CO>[CH3:1][C:2]([C:3]1[N:13]2[CH2:12][CH2:17][CH:16]([C:18]3[O:22][N:21]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:19]=3)[CH2:15][C:14]2=[N:6][N:5]=1)([CH3:9])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 62678395HCID 62678395, compoundHCID 67297399HCID 67297399, compound

Product 1

HCID 67300411HCID 67300411, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reflux 2,2-dimethyl-butyric acid hydrazide (0.053 g, 0.48 mmol) and 5-(2-methoxy-3,4,5,6-tetrahydropyridin-4-yl)-3-phenyl-1,2,4-oxadiazole (0.1 g, 0.39 mmol) in methanol (1.55 mL) overnight. Remove the methanol under reduced pressure and replace with acetic acid (2 mL). Reflux the reaction for 3 hours and pour over aqueous saturated sodium bicarbonate. Extract with dichloromethane and dry the organics over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography eluting with 5-15% ethyl acetate in dichloromethane. Recrystallize from ethyl acetate and hexane to afford the title compound as a crystalline solid (0.078 g). Mass spectrum (m/z): 338 (M+1).

Workup

  1. customRemove the methanol under reduced pressure
  2. temperatureReflux
  3. customthe reaction for 3 hours
  4. extractionExtract with dichloromethane
  5. dry with materialdry the organics over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the resulting residue by flash chromatography
  9. washeluting with 5-15% ethyl acetate in dichloromethane
  10. customRecrystallize from ethyl acetate and hexane

Sources & evidence

ORD record
ord-bd2f6f3759404aba87149905516260ba
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

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