N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide → N-(6-(oxazol-2-yl)-5-(pyridin-4-yl)pyrazin-2-yl)cyclopropanecarboxamide

HRID 1710701Notes

Reaction equation

HRID 1710701 reaction equation
[Cl-].[O:2]1[CH:6]=[CH:5][N:4]=[C:3]1[Zn+].Cl[C:9]1[N:14]=[C:13]([NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:12]=[N:11][C:10]=1[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:9]1[N:14]=[C:13]([NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:12]=[N:11][C:10]=1[C:21]1[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 59457608N-(6-Chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamideHCID 178479834HCID 178479834, compound2×

Product 1

HCID 16071780N-(6-(oxazol-2-yl)-5-(pyridin-4-yl)pyrazin-2-yl)cyclopropanecarboxamideYield 26%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

(1,3-Oxazol-2-yl)zinc chloride (0.33M in THF, 9.3 mL, 3.06 mmol) was added to a solution of N-(6-chloro-5-pyridin-4-ylpyrazin-2-yl)cyclopropanecarboxamide (Preparation 8, 280 mg, 1.02 mmol) in THF (2 mL) and the mixture was degassed Pd(PPh3)4 (118 mg, 0.102 mmol, 10 mol %) was added and degassing was repeated. The reaction mixture was heated to 90° C. in a sealed tube and stirred overnight. The mixture was cooled and more (1,3-oxazol-2-yl)zinc chloride (0.33M, 5.0 mL, 1.65 mmol) and Pd(PPh3)4 (90 mg, 8 mol %) were added and the mixture was degassed and heated to 90° C. overnight. The reaction mixture was cooled and concentrated. The residue was purified by flash silica gel chromatography (dichloromethane/methanol 98:2) to give the title compound (80 mg, 26%) as a pale yellow solid.

Workup

  1. additionwas added
  2. customdegassing
  3. temperatureThe mixture was cooled
  4. customthe mixture was degassed
  5. temperatureheated to 90° C. overnight
  6. temperatureThe reaction mixture was cooled
  7. concentrationconcentrated
  8. customThe residue was purified by flash silica gel chromatography (dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-7ea27d3422254ab0bdb0aa294d61ed73
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

Loading…