HCID 178429387, compound → HCID 178429385, compound

HRID 707392Notes

Reaction equation

HRID 707392 reaction equation
C([O:8][C@@H:9]1[CH2:12][C@H:11]([N:13]2[C:17]3=[N:18][CH:19]=[CH:20][N:21]=[C:16]3[C:15]([CH3:23])([CH3:22])[C:14]2=[O:24])[CH2:10]1)C1C=CC=CC=1>CO.O[Pd]O>[OH:8][C@@H:9]1[CH2:12][C@H:11]([N:13]2[C:17]3=[N:18][CH:19]=[CH:20][N:21]=[C:16]3[C:15]([CH3:22])([CH3:23])[C:14]2=[O:24])[CH2:10]1

Participants

4

Reactant 1

HCID 178429387HCID 178429387, compound

Product 1

HCID 178429385HCID 178429385, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 178526213HCID 178526213, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(cis-3-(benzyloxy)cyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.205 g, 0.634 mmol), and dihydroxypalladium (0.092 g, 0.655 mmol) in MeOH (5 mL) was hydrogenated at room temperature under H, balloon overnight. The catalyst was filtered off, the filtrate was concentrated, and purified by ISCO (65% EtOAc/Hexanes) to give the title compound (55 mg, 37%). MS (M+1): 234.1.

Workup

  1. customwas hydrogenated at room temperature under H, balloon overnight
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by ISCO (65% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-e12dc41d8929432f9f2c4de70dbfe603
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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