3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-acrylic acid ethyl ester → 3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-propionic acid ethyl ester

HRID 732101

Reaction equation

HRID 732101 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])=[CH:6][C:7]1[N:11]([CH:12]2[CH2:14][CH2:13]2)[C:10]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[N:9][N:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([CH3:21])[CH2:6][C:7]1[N:11]([CH:12]2[CH2:14][CH2:13]2)[C:10]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[N:9][N:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 670709853-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-acrylic acid ethyl ester

Product 1

HCID 578380023-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-acrylic acid ethyl ester (5.76 g, 19.3 mmol) was hydrogenated with 10% Pd/C (3.0 g) in EtOH (100 ml) o.n. The reaction mixture was filtered and concentrated. The residue was triturated with hex. to give the title compound in 3.1 g (53%) yield. 1H-NMR: 8.76 (d, 2H), 7.73 (d, 2H), 4.14(m, 2H), 3.35 (m, 3H), 2.88 (q, 1H), 1.39 (d, 3H), 1.25 (t, 3H), 1.18 (m, 2H) and 0.73 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was triturated with hex

Sources & evidence

ORD record
ord-8ee6184536884dfdb437ab35dae7039b
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

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