Acetic Acid → HCID 66778551, compound

HRID 406402Notes

Reaction equation

HRID 406402 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]4)=[C:19]([O:29][CH3:30])[N:18]=3)[N:16]=[C:10]2[CH:9]1[C:31]1[CH:32]=[C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=[CH:35][CH:36]=1)C1C=CC=CC=1.C(O)(=O)C.[H][H].C(OCC)(=O)C>CO.[OH-].[Pd+2].[OH-]>[C:33]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:34]=[CH:35][CH:36]=[C:31]([CH:9]2[NH:8][CH2:13][CH2:12][N:11]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([N:23]5[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]5)=[C:19]([O:29][CH3:30])[N:18]=4)[N:16]=[C:10]23)[CH:32]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 66778949HCID 66778949, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66778551HCID 66778551, compoundYield 9.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7-benzyl-8-biphenyl-3-yl-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine (541 mg) and acetic acid (1.32 ml) in methanol (52 ml) was added 20% palladium hydroxide (743 mg) and the reaction mixture was stirred at room temperature in a hydrogen atmosphere for 4 days. After the reaction atmosphere was replaced with nitrogen, ethyl acetate was added to the reaction mixture. The catalyst was removed by filtration by Celite. The filtrate was concentrated under reduced pressure and the residue was purified by NH silica gel column chromatography to obtain the title compound (45 mg) and the raw material. (291 mg)

Workup

  1. customAfter the reaction atmosphere
  2. additionwas added to the reaction mixture
  3. customThe catalyst was removed by filtration by Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-ebb911b538774363aacecf85cef13b42
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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