Trifluoroacetic acid → rac-N-(2-Amino-2-methylpentyl)-2,5-dimethyl-7-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]pyrazolo[1,5-a]pyridine-3-carboxamide

HRID 1486354Notes

Reaction equation

HRID 1486354 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:39])([CH2:36][CH2:37][CH3:38])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:35])=[N:15][N:16]2[C:21]([O:22][CH2:23][CH2:24][CH:25]([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:20][C:19]([CH3:34])=[CH:18][C:17]=12)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:39])([CH2:36][CH2:37][CH3:38])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:35])=[N:15][N:16]2[C:21]([O:22][CH2:23][CH2:24][CH:25]([C:30]([F:33])([F:32])[F:31])[C:26]([F:27])([F:28])[F:29])=[CH:20][C:19]([CH3:34])=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 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 Ester

Product 1

HCID 117864673rac-N-(2-Amino-2-methylpentyl)-2,5-dimethyl-7-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]pyrazolo[1,5-a]pyridine-3-carboxamideYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 30 mg (0.051 mmol) of 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 (Example 142A) in 2 ml of dichloromethane was admixed with trifluoroacetic acid (0.117 ml). The reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated off under reduced pressure and the residue was partitioned between dichloromethane and water. The organic phase was removed and concentrated under reduced pressure, and the residue was purified by preparative HPLC chromatography (Method 21), which gave 1.68 mg (7% yield) of the target compound.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was partitioned between dichloromethane and water
  3. customThe organic phase was removed
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by preparative HPLC chromatography (Method 21), which

Sources & evidence

ORD record
ord-33fd661913db453cb0515f82846f6688
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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