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

HRID 1486353Notes

Reaction equation

HRID 1486353 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[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[CH:20][C:19](C)=[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[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[CH:20][CH:19]=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 117864595rac-{1-[({7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Product 1

HCID 121434525rac-N-(2-Amino-2-methylpentyl)-7-[(2-chloro-6-fluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxamideYield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 40 mg (0.073 mmol) of rac-{1-[({7-[(2-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 138A) in 2 ml of dichloromethane was admixed with 0.113 ml of trifluoroacetic acid. The resulting mixture was stirred at room temperature for 18 hours and then heated to 40° C. Further trifluoroacetic acid (0.169 ml) was added in portions over the course of 3 hours. The reaction mixture was concentrated under reduced pressure and the remaining residue was purified by preparative HPLC chromatography (Method 21), which gave 11.0 mg (33% yield) of the target compound.

Workup

  1. temperatureheated to 40° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe remaining residue was purified by preparative HPLC chromatography (Method 21), which

Sources & evidence

ORD record
ord-17fa7b91a30b456dbc45fa0401275c1c
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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