Dichloromethane methanol → HCID 90017228, compound

HRID 1054959Notes

Reaction equation

HRID 1054959 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH:11]=[CH:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]([CH2:21][CH3:22])[CH3:20])[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:23])=[N:4][CH:3]=1.C(Cl)Cl.CO>[Pd].CO>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:17]([CH3:18])[N:16]=[C:15]([N:19]([CH2:21][CH3:22])[CH3:20])[N:14]=3)[N:10]=[C:6]2[C:5]([CH3:23])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 131736339HCID 131736339, compound

Product 1

HCID 90017228HCID 90017228, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 5-(2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)vinyl)-N-ethyl-N,1-dimethyl-1H-1,2,4-triazol-3-amine (7 mg, 22.4 μmol, Eq: 1.00) and palladium on carbon 10% (4.77 mg, 4.48 μmol, Eq: 0.2) in methanol (1 ml) was stirred for 14 hours at 25° C. under hydrogen atmosphere. TLC (CH2Cl2/MeOH 19:1/UV 254 nm) showed complete reaction (spot to spot). palladium was filtered off and the filtrate was evaporated and applied on silica gel. Purification by column chromatography over 10 g SiO2 using ethyl acetate/methanol (0-10% MeOH) as eluent to give {5-[2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-ethyl]-1-methyl-1H-[1,2,4]triazol-3-yl}-ethyl-methyl-amine (3.5 mg, 49.7%) as off-white solid

Workup

  1. customreaction (spot to spot)
  2. filtrationpalladium was filtered off
  3. customthe filtrate was evaporated
  4. customPurification by column chromatography over 10 g SiO2

Sources & evidence

ORD record
ord-139673b8cfaf48f58004634a14e57088
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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