Cesium carbonate → rac-[1-[({2,5-Dimethyl-7-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]pyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

HRID 1486308Notes

Reaction equation

HRID 1486308 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([CH3:28])([CH2:25][CH2:26][CH3:27])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:24])=[N:15][N:16]2[C:21]([OH:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][CH2:38][CH:39]([C:44]([F:47])([F:46])[F:45])[C:40]([F:43])([F:42])[F:41]>CN(C=O)C>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([CH3:28])([CH2:25][CH2:26][CH3:27])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:24])=[N:15][N:16]2[C:21]([O:22][CH2:37][CH2:38][CH:39]([C:40]([F:41])([F:42])[F:43])[C:44]([F:45])([F:47])[F:46])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=12)=[O:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27779984-Bromo-1,1,1-trifluoro-2-(trifluoromethyl)butaneHCID 178444850HCID 178444850, compound

Product 1

HCID 117864622rac-[1-[({2,5-Dimethyl-7-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]pyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl EsterYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 40 mg (0.10 mmol) of rac-[1-{[7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carbonyl)amino]}-1-methylbutyl)carbamic acid tert-butyl ester (Example 141A) in 1 ml of DMF was admixed with 65 mg (0.2 mmol) of caesium carbonate and 78 mg (0.3 mmol) of 4-bromo-1,1,1-trifluoro-2-(trifluoromethyl)butane (CAS: 203303-02-0). The reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated off under reduced pressure. The residue was partitioned between dichloromethane and water, the phases were separated and the organic phase was concentrated under reduced pressure, which gave 55 mg (51% yield, 54% pure) of the target compound, which was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customThe residue was partitioned between dichloromethane and water
  3. customthe phases were separated
  4. concentrationthe organic phase was concentrated under reduced pressure, which
  5. customgave 55 mg (51% yield, 54% pure) of the target compound, which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c940720b113f4f488b60ca635aef5b44
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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