2-Chloro-6-fluorobenzoic acid → 3-Butyl-8-chloro-1-{4-[5-(2-chloro-6-fluorophenyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097693Notes

Reaction equation

HRID 1097693 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:16]1[C:24]2[N:23]=[C:22]([Cl:25])[NH:21][C:20]=2[C:19](=[O:26])[N:18]([CH2:27][CH2:28][CH2:29][CH2:30]/[C:31](=[N:34]/[H])/[NH:32]O)[C:17]1=[O:36])[CH2:13][CH2:14][CH3:15]>CS(C)=O>[CH2:12]([N:16]1[C:24]2[N:23]=[C:22]([Cl:25])[NH:21][C:20]=2[C:19](=[O:26])[N:18]([CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[N:32]=[C:4]([C:3]3[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])[O:6][N:34]=2)[C:17]1=[O:36])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 679472-Chloro-6-fluorobenzoic acidHCID 178506472HCID 178506472, compound

Product 1

HCID 593956083-Butyl-8-chloro-1-{4-[5-(2-chloro-6-fluorophenyl)-1,2,4-oxadiazol-3-yl]butyl}-3,7-dihydro-1H-purine-2,6-dioneYield 5.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-6-fluorobenzoic acid (44 mg, 0.25 mmol) and CDl (45 mg, 0.28 mmol) were stirred in anhydrous DMSO (0.9 ml) at rt for 1 h. (1Z)-5-(3-Butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)-N-hydroxypentanimidamide (100 mg, 0.28 mmol) was added and the mixture was stirred at 90° C. for 16 h. The mixture was purified by MDAP. The product fraction was combined and concentrated to give the title compound as a white solid (6.4 mg, 5%).

Workup

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

Sources & evidence

ORD record
ord-b5def01efac74724ac06b89cb61e05de
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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