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

HRID 1486347Notes

Reaction equation

HRID 1486347 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:37])([CH2:34][CH2:35][CH3:36])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:33])=[N:15][N:16]2[C:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=3[F:31])=[CH:20][C:19]([CH3:32])=[CH:18][C:17]=12)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:37])([CH2:34][CH2:35][CH3:36])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:33])=[N:15][N:16]2[C:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=3[F:31])=[CH:20][C:19]([CH3:32])=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117864617rac-{1-[({7-[(2,3-Difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Product 1

HCID 117864537rac-N-(2-Amino-2-methylpentyl)-7-[(2,3-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 35 mg (0.066 mmol) of rac-{1-[({7-[(2,3-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 118A) in 2 ml of dichloromethane was admixed with 0.079 ml (1.03 mmol) of trifluoroacetic acid. The resulting solution was stirred at room temperature overnight. The solvent was drawn off under reduced pressure and the residue was purified by preparative HPLC chromatography (Method 21), which gave 6 mg (27% of theory) of the target compound.

Workup

  1. customthe residue was purified by preparative HPLC chromatography (Method 21), which
  2. customgave 6 mg (27% of theory) of the target compound

Sources & evidence

ORD record
ord-56832859d09548e4ab080101f8a48949
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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