Benzoic Acid → 8-Chloro-1-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)butyl]-3-propyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097692Notes

Reaction equation

HRID 1097692 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[NH:19][C:18]2[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:23][CH2:24]/[C:25](=[N:28]/[H])/[NH:26]O)[C:15](=[O:30])[N:14]([CH2:31][CH2:32][CH3:33])[C:13]=2[N:12]=1>CS(C)=O>[Cl:10][C:11]1[NH:19][C:18]2[C:17](=[O:20])[N:16]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[N:26]=[C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[O:9][N:28]=3)[C:15](=[O:30])[N:14]([CH2:31][CH2:32][CH3:33])[C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 178506471HCID 178506471, compound

Product 1

HCID 593957668-Chloro-1-[4-(5-phenyl-1,2,4-oxadiazol-3-yl)butyl]-3-propyl-3,7-dihydro-1H-purine-2,6-dioneYield 2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Benzoic acid (9 mg, 0.074 mmol) and CDl (13 mg, 0.081 mmol) were stirred in anhydrous DMSO (0.9 ml) at rt for 1 h. (1Z)-5-(8-Chloro-2,6-dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (28 mg, 0.081 mmol) was added and the mixture was stirred at 80° C. for 4 h. The mixture was purified by MDAP to give the title compound as a white solid (0.6 mg, 2%).

Workup

  1. additionwas added
  2. customThe mixture was purified by MDAP

Sources & evidence

ORD record
ord-a14d9b82d5804d2c9787ccc911fda6c4
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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