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

HRID 1486351Notes

Reaction equation

HRID 1486351 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]([C:31]#[N: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]([C:31]#[N: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 117864620{1-[({7-[(3-Cyano-2,6-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 117864662rac-N-(2-Amino-2-methylpentyl)-7-[(3-cyano-2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude rac-{1-[({7-[(3-cyano-2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 126A) in 4 ml of dichloromethane was admixed with 2 ml of trifluoroacetic acid. The resulting solution was stirred at room temperature for 3 h. The solvent was drawn off under reduced pressure and the residue was purified by preparative HPLC chromatography (Method 21), which gave 4.5 mg (5% of theory over 2 stages) of the target compound.

Workup

  1. customthe residue was purified by preparative HPLC chromatography (Method 21), which
  2. customgave 4.5 mg (5% of theory over 2 stages) of the target compound

Sources & evidence

ORD record
ord-bc1de5eb4d5c49778dbe5593c410a71f
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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