HCID 66604287, compound → HCID 66604162, compound

HRID 1398227Notes

Reaction equation

HRID 1398227 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:21]2[N:25]3[CH2:26][CH2:27][CH2:28][C:29]([C:39]([OH:42])([CH3:41])[CH3:40])([O:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[C:33]([F:38])[CH:32]=4)[C:24]3=[N:23][N:22]=2)[CH:12]=[CH:13][C:14]=1[C:15]1[O:19][C:18]([CH3:20])=[N:17][CH:16]=1)C1C=CC=CC=1>CO.[C].[Pd]>[F:38][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=1[F:37])[O:30][C:29]1([C:39]([OH:42])([CH3:41])[CH3:40])[CH2:28][CH2:27][CH2:26][N:25]2[C:21]([C:11]3[CH:12]=[CH:13][C:14]([C:15]4[O:19][C:18]([CH3:20])=[N:17][CH:16]=4)=[C:9]([OH:8])[CH:10]=3)=[N:22][N:23]=[C:24]12

Participants

4

Reactant 1

HCID 66604287HCID 66604287, compound

Product 1

HCID 66604162HCID 66604162, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-{3-[3-(benzyloxy)-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4-difluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol (100 mg) and 5% palladium-carbon (100 mg) in methanol (1.5 mL) was stirred at room temperature for 45 min under a hydrogen atmosphere. The mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (58.1 mg).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d2e3e626d4fa4d578bdcaef2b77cc8f2
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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