Acetic Acid → 4-[5-Amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one

HRID 1959443Notes

Reaction equation

HRID 1959443 reaction equation
C(OC([N:8]([C:16]1[C:21]([C:22]2[O:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:25][N:26]=2)=[N:20][C:19]([C:33]2[CH2:42][CH2:41][C:36]3(OCC[O:37]3)[CH2:35][CH:34]=2)=[CH:18][N:17]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.CC(O)=O.O.[OH-].[Na+]>CCOC(C)=O>[NH2:8][C:16]1[N:17]=[CH:18][C:19]([C:33]2[CH2:42][CH2:41][C:36](=[O:37])[CH2:35][CH:34]=2)=[N:20][C:21]=1[C:22]1[O:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:25][N:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66744206tert-butyl N-tert-butoxycarbonyl-N-[5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]carbamate

Product 1

HCID 667447634-[5-Amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-oneYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl N-tert-butoxycarbonyl-N-[5-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]carbamate in (40 mg, 0.069 mmol) AcOH (832 mg, 788 μL, 13.85 mmol) and H2O (50 mg, 50 μL, 2.8 mmol) was heated at 80° C. for 2 h. The reaction mixture was diluted with 10 ml of EtOAc and pH was adjusted to 8 with 1N NaOH. The reaction mixture was washed with 20 ml of NaHCO3. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to obtain 4-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclohex-3-en-1-one (19 mg, 82%), which was used as crude for the next step. LC/MS m/z 334.0 [M+H]+.

Workup

  1. washThe reaction mixture was washed with 20 ml of NaHCO3
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c36baa8898d43be85d0a2108ca411ed
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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