HCID 67330476, compound → HCID 58374619, compound

HRID 533179Notes

Reaction equation

HRID 533179 reaction equation
N1C=CC=C(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:20]4[N:21]=[C:22]([NH:24][C:25]([CH:27]5[CH2:29][CH2:28]5)=[O:26])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)C=1>CO.[Pd]>[N:20]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:20]3[N:21]=[C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])[N:23]=[C:19]3[CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 67330476HCID 67330476, compound

Product 1

HCID 58374619HCID 58374619, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Cyclopropanecarboxylic acid{5-[4-((E)-2-pyridin-3-yl-vinyl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide (320 mg, 0.84 mol) was dissolved in 10 mL MeOH. Pd/C (50 mg) was added and the reaction is put under H2 at normal pressure. The reaction was stirred for 2 hrs. The reaction mixture was filtered through Celite®. The organic solvent was removed under pressure. NaHCO3 saturated solution was added to resulting mixture. The compound was extracted with EtOAc. The organic phase was dried over MgSO4, filtered and removed under vacuum to afford the title compound in 100% yield.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customThe organic solvent was removed under pressure
  3. additionNaHCO3 saturated solution was added
  4. customto resulting mixture
  5. extractionThe compound was extracted with EtOAc
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. customremoved under vacuum

Sources & evidence

ORD record
ord-e14bba16042e470fb592a0c36a3e60bd
Source dataset
uspto-grants-2014_10
Patent number
US08853240B2

Reaction notes

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