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

HRID 1486348Notes

Reaction equation

HRID 1486348 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:35])([CH2:32][CH2:33][CH3:34])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:31])=[N:15][N:16]2[C:21]([O:22][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:20][C:19]([CH3:30])=[CH:18][C:17]=12)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:35])([CH2:32][CH2:33][CH3:34])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:31])=[N:15][N:16]2[C:21]([O:22][CH2:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:20][C:19]([CH3:30])=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117864550rac-[1-({[7-(Cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

Product 1

HCID 117864707rac-N-(2-Amino-2-methylpentyl)-7-(cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 40 mg (0.047 mmol, 59% pure) of rac-[1-({[7-(cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic acid tert-butyl ester (Example 121A) in 2 ml of dichloromethane was admixed with 0.072 ml (0.94 mmol) of trifluoroacetic acid. The resulting solution was stirred at room temperature overnight. 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 8 mg (43% of theory) of the target compound.

Workup

  1. customthe residue was purified by preparative HPLC chromatography (Method 21), which
  2. customgave 8 mg (43% of theory) of the target compound

Sources & evidence

ORD record
ord-4712686640ff4605b984ad9d347e19d4
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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