HCID 86614853, compound → HCID 86614852, compound

HRID 1863970Notes

Reaction equation

HRID 1863970 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:3]=1[CH2:4][C@@H:5]([NH:23][C:24](=[O:26])[CH3:25])[CH2:6][C:7]1[N:11]2[CH:12]=[CH:13][C:14]3[N:15]([N:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=3)[C:10]2=[N:9][N:8]=1.[H][H]>[Pd].COCCO>[F:1][C:2]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:3]=1[CH2:4][C@@H:5]([NH:23][C:24](=[O:26])[CH3:25])[CH2:6][C:7]1[N:11]2[CH2:12][CH2:13][C:14]3[N:15]([N:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=3)[C:10]2=[N:9][N:8]=1

Participants

5

Reactant 2

HCID 86614853HCID 86614853, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86614852HCID 86614852, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 52.1 mg (0.114 mmol) of N-{(1R)-1-(2,4,5-trifluorobenzyl)-2-[8-(trifluoromethyl)bis[1,2,4]triazolo[1,5-c:4′,3′-a]pyrimidin-3-yl]ethyl}acetamide, 52 mg of 10% palladium on carbon, and 5 mL of 2-methoxyethanol was shaken with hydrogen (52 psi) for 26 h. The catalyst was removed by filtration through Celite, and the filtrate was concentrated to dryness. The residue was purified by preparative thin-layer chromatography on silica gel (three successive developments in 92.5:7.5 dichloromethane:methanol) to provide the title compound. LC-MS 460 (M+1).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by preparative thin-layer chromatography on silica gel (three successive developments in 92.5:7.5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-f130d1a640f44ad889568e60b65ab0cf
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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