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

HRID 1486350Notes

Reaction equation

HRID 1486350 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][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[C:25]=3[F:33])=[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][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[C:25]=3[F:33])=[CH:20][C:19]([CH3:34])=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117864681rac-{1-[({7-[(2,6-Difluoro-3-methoxybenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Product 1

HCID 117864666rac-N-(2-Amino-2-methylpentyl)-7-[(2,6-difluoro-3-methoxybenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

rac-{1-[({7-[(2,6-Difluoro-3-methoxybenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]-pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 125A) in 4 ml of dichloromethane was admixed with 3 ml of trifluoroacetic acid. The resulting solution was stirred at room temperature for 3 h. 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 10 mg (11% of theory, over 2 stages) of the target compound.

Workup

  1. customthe residue was purified by preparative HPLC chromatography (Method 21), which
  2. customgave 10 mg (11% of theory, over 2 stages) of the target compound

Sources & evidence

ORD record
ord-24ce3d9407c14b2fbcf99ce9503f4636
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

Loading…