Triethylamine → HCID 90025845, compound

HRID 1054967Notes

Reaction equation

HRID 1054967 reaction equation
Cl[C:2]1[CH:3]=[CH:4][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].C(N(CC)CC)C>[Pd].C(O)C>[CH3:8][C:7]1[N:6]2[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]=[C:5]2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 123709604HCID 123709604, compound

Product 1

HCID 90025845HCID 90025845, compoundYield 110.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6-chloro-5-methyl-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridine (5 mg, 14.5 μmol, Eq: 1.00), palladium on carbon (10.0 mg, 94.0 μmol, Eq: 6.46) and triethylamine (0.02 ml) in ethanol (3 ml) was stirred 1 h under hydrogen (1 atm). The mixture was filtered over Celite and then concentrated to an oil. The residue was dissolved in DCM (15 ml) and Na2CO3 (50 mg) was added. The mixture was stirred for 5 min and then filtered over Celite and concentrated to give the desired product (5 mg) as a colorless oil. MS: m/z=312.3 (M+H+)

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationconcentrated to an oil
  3. dissolutionThe residue was dissolved in DCM (15 ml)
  4. additionNa2CO3 (50 mg) was added
  5. stirringThe mixture was stirred for 5 min
  6. filtrationfiltered over Celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8bf19a6f4ace43e5a2fedce47535f927
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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