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

HRID 1486349Notes

Reaction equation

HRID 1486349 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:33])([CH2:30][CH2:31][CH3:32])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:29])=[N:15][N:16]2[C:21]([O:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:20][C:19]([CH3:28])=[CH:18][C:17]=12)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:33])([CH2:30][CH2:31][CH3:32])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:29])=[N:15][N:16]2[C:21]([O:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:20][C:19]([CH3:28])=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 121434556rac-[1-({[2,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

Product 1

HCID 117864654rac-N-(2-Amino-2-methylpentyl)-2,5-dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 80 mg (0.091 mmol, 54% pure) of rac-[1-({[2,5-dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic acid tert-butyl ester (Example 124A) in 4 ml of dichloromethane was admixed with 0.140 ml (1.82 mmol) of trifluoroacetic acid. The resulting solution was stirred at room temperature overnight. After the reaction had ended, the solvent was drawn off under reduced pressure and the residue was purified by preparative HPLC chromatography (Method 21), which gave 17 mg (50% of theory) of the target compound.

Workup

  1. customthe residue was purified by preparative HPLC chromatography (Method 21), which
  2. customgave 17 mg (50% of theory) of the target compound

Sources & evidence

ORD record
ord-cd6224f27dd14decba5feb7635f1200a
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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