HCID 44434209, compound → HCID 4999172, compound

HRID 644284Notes

Reaction equation

HRID 644284 reaction equation
C(OC(N1CCC(OC2C=C(C(C)(C)C)C=CC=2C(N[C:20]2[CH:35]=[CH:34][CH:33]=[CH:32][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=O)CC1)=O)(C)(C)C>Cl.O1CCOCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:22](=[O:23])[C:21]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:20]=2)=[N:26][CH:27]=1

Participants

4

Reactant 1

HCID 44434209HCID 44434209, compound

Product 1

HCID 4999172HCID 4999172, compoundYield 219.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(tert-butyl)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (1.57 g, 2.58 mmol) was dissolved in 20 mL of a 4 N HCl in dioxane solution at room temperature, resulting in a modest evolution of gas. After 1 hour stirring at room temperature, the solvent and HCl gas were evaporated in vacuo, then the resulting white solid was resuspended in 75 mL 2:1 EtOAc:dichloromethane and evaporated a second time. The pasty white solid was dissolved in a solution of K2 CO3 (11.2 g) in water (75 mL), dichloromethane was added (75 mL), and the mixture vigorously stirred overnight. The mixture was partitioned, the aqueous layer back-extracted twice with dichloromethane, then the combined organic layers washed with brine. The organic layer was dried and concentrated in vacuo to provide 2-[4-tert-butyl)-2-(piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (1.32 g, 100%) as an off-white crystalline solid.

Workup

  1. customresulting in a modest evolution of gas
  2. customthe solvent and HCl gas were evaporated in vacuo
  3. customdichloromethane and evaporated a second time
  4. dissolutionThe pasty white solid was dissolved in a solution of K2 CO3 (11.2 g) in water (75 mL), dichloromethane
  5. additionwas added (75 mL)
  6. customthe mixture vigorously stirred overnight
  7. customThe mixture was partitioned
  8. extractionthe aqueous layer back-extracted twice with dichloromethane
  9. washthe combined organic layers washed with brine
  10. customThe organic layer was dried
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ca3178eef624d99b3625255af48f0fb
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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