HCID 71185992, compound → HCID 71203184, compound

HRID 633636Notes

Reaction equation

HRID 633636 reaction equation
Cl[C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C:7]2[N:8]=[C:9]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:10]3[N:15]=[C:14]([C:16]4[CH:26]=[C:25]([CH3:27])[C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[C:18]([CH3:28])[CH:17]=4)[O:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1>[Pd]>[CH2:6]([C:7]1[N:8]=[C:9]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:10]2[N:15]=[C:14]([C:16]3[CH:26]=[C:25]([CH3:27])[C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[C:18]([CH3:28])[CH:17]=3)[O:13][C:11]=2[N:12]=1)[C:5]1[CH:4]=[CH:3][CH:2]=[CH:34][CH:33]=1

Participants

3

Reactant 1

HCID 71185992HCID 71185992, compound

Product 1

HCID 71203184HCID 71203184, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

10 mg of palladium on carbon (10%) were added to a solution of 50 mg of {4-[5-(4-chlorobenzyl)-7-isobutyloxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetic acid, and the mixture was hydrogenated at 5 bar overnight. Three times, another 10 mg of palladium on carbon (10%) were added and the mixture was in each case hydrogenated for a day. For work-up, the catalyst was filtered off through Celite and the solution obtained was concentrated. The residue was purified by HPLC. This gave 7 mg (18%) of the title compound.

Workup

  1. customwas hydrogenated at 5 bar overnight
  2. waithydrogenated for a day
  3. filtrationFor work-up, the catalyst was filtered off through Celite
  4. customthe solution obtained
  5. concentrationwas concentrated
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-4009d958185743968d2c79f5e0884749
Source dataset
uspto-grants-2016_04
Patent number
US09321787B2

Reaction notes

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