Trifluoroacetic acid → rac-N-(2-Amino-2-methylpentyl)-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxamide

HRID 1486352Notes

Reaction equation

HRID 1486352 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:36])([CH2:33][CH2:34][CH3:35])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:32])=[N:15][N:16]2[C:21]([O:22][CH2:23][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])=[CH:20][CH:19]=[CH:18][C:17]=12)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:36])([CH2:33][CH2:34][CH3:35])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:32])=[N:15][N:16]2[C:21]([O:22][CH2:23][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])=[CH:20][CH:19]=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 121434576rac-{1-[({7-[(2,6-Difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Product 1

HCID 117864717rac-N-(2-Amino-2-methylpentyl)-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 45 mg (0.046 mmol, 53% pure) of rac-{1-[({7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 131A) in 4 ml of dichloromethane was admixed with 0.5 ml (6.49 mmol) of trifluoroacetic acid. The resulting solution was stirred at room temperature for 2 h. The solvent was drawn off under reduced pressure and the residue was purified by preparative HPLC chromatography (Method 21), which gave 6.5 mg (34% yield) of the target compound as a white powder.

Workup

  1. customthe residue was purified by preparative HPLC chromatography (Method 21), which

Sources & evidence

ORD record
ord-1d187ee8f49a4b4e94420e7cd13c9609
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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