HCID 90017406, compound → HCID 90026082, compound

HRID 1054994Notes

Reaction equation

HRID 1054994 reaction equation
[CH:1]1([N:4]([CH2:24][CH3:25])[C:5]2[N:9]=[C:8](/[CH:10]=[CH:11]/[C:12]3[N:22]=[C:15]4[C:16]([CH3:21])=[N:17][CH:18]=[C:19]([CH3:20])[N:14]4[N:13]=3)[N:7]([CH3:23])[N:6]=2)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([N:4]([C:5]2[N:9]=[C:8]([CH2:10][CH2:11][C:12]3[N:22]=[C:15]4[C:16]([CH3:21])=[N:17][CH:18]=[C:19]([CH3:20])[N:14]4[N:13]=3)[N:7]([CH3:23])[N:6]=2)[CH2:24][CH3:25])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 90017406HCID 90017406, compound

Product 1

HCID 90026082HCID 90026082, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (E)-N-cyclopropyl-5-(2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)vinyl)-N-ethyl-1-methyl-1H-1,2,4-triazol-3-amine (75 mg, 222 μmol, Eq: 1.00) and palladium on carbon 10% (11.8 mg, 11.1 μmol, Eq: 0.05) in methanol (15 ml) was stirred for 5 hours at 25° C. under hydrogen atmosphere. The catalyst was filtered off, the filtrate was evaporated affording cyclopropyl-{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-amine (65 mg, 86.2%) as a light yellow viscous oil. MS: m/z=341.5 (M+H+)

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-039091ad00a04db69c9900d7f391e233
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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