N'-Hydroxybenzenecarboximidamide → 3-Butyl-8-chloro-1-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)butyl]-3,7-dihydro-1H-purine-2,6-dione

HRID 1097702Notes

Reaction equation

HRID 1097702 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4].[C:24](=[N:32]O)([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[O:22][N:32]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:31]=2)[C:6]1=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 69186N'-HydroxybenzenecarboximidamideHCID 59395495HCID 59395495, compound

Product 1

HCID 593954823-Butyl-8-chloro-1-[4-(3-phenyl-1,2,4-oxadiazol-5-yl)butyl]-3,7-dihydro-1H-purine-2,6-dioneYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CDl (0.98 g, 6.1 mmol) was added to a solution of 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoic acid (1.89 g, 5.5 mmol) in DMF (15 ml) and stirred under nitrogen for 1.5 h. Benzamidoxime (0.91 g, 6.1 mmol) was added and the mixture stirred at 110° C. overnight. The reaction mixture was partitioned between EtOAc and 2M HCl. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. The crude product was crystallised from methanol and then further purified using the Companion™ system and a gradient elution from cyclohexane to EtOAc. Product containing fractions were combined and evaporated to give the title compound as a white solid (850 mg).

Workup

  1. stirringthe mixture stirred at 110° C. overnight
  2. customThe reaction mixture was partitioned between EtOAc and 2M HCl
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was crystallised from methanol
  8. customfurther purified
  9. washa gradient elution from cyclohexane to EtOAc
  10. additionProduct containing fractions
  11. customevaporated

Sources & evidence

ORD record
ord-540a3cfe341b4de5988fdf7f90c23174
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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