HCID 90026501, compound → HCID 90033975, compound

HRID 1054971Notes

Reaction equation

HRID 1054971 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]2[N:6]([N:9]=[C:10](/[CH:12]=[CH:13]/[C:14]3[N:18]([CH3:19])[N:17]=[C:16]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:15]=3)[N:11]=2)[C:7]=1[CH3:8]>[Pd].C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:25])[C:5]2[N:6]([N:9]=[C:10]([CH2:12][CH2:13][C:14]3[N:18]([CH3:19])[N:17]=[C:16]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:15]=3)[N:11]=2)[C:7]=1[CH3:8]

Participants

4

Reactant 1

HCID 90026501HCID 90026501, compound

Product 1

HCID 90033975HCID 90033975, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate was added to (E)-6-chloro-5,8-dimethyl-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridine (15 mg). Palladium (5 wt. %) on barium sulfate (20 mg) was added. The mixture was stirred for 5 h under a hydrogen atmosphere and then filtered over Celite. The mixture was concentrated and purified by preparative HPLC to give the desired product (10.2 mg, 67.8%) as a light yellow powder. MS: m/z=360.5 (M+H+)

Workup

  1. filtrationfiltered over Celite
  2. concentrationThe mixture was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d34125dd7eda4c91ba32a63544f15797
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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