Trifluoroacetic acid → HCID 117864667, compound

HRID 1486358Notes

Reaction equation

HRID 1486358 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:38])([CH2:35][CH2:36][CH3:37])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:34])=[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[F:31])=[CH:20][C:19]([CH2:32][CH3:33])=[CH:18][C:17]=12)=[O:12])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:38])([CH2:35][CH2:36][CH3:37])[CH2:9][NH:10][C:11]([C:13]1[C:14]([CH3:34])=[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[F:31])=[CH:20][C:19]([CH2:32][CH3:33])=[CH:18][C:17]=12)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117864551HCID 117864551, compound

Product 1

HCID 117864667HCID 117864667, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 19 mg (0.033 mmol, 95% purity) of rac-{1-[({7-[(2,6-difluorobenzyl)oxy]-5-ethyl-2-methylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 169A) in 1 ml of dichloromethane was admixed with 0.15 ml of trifluoroacetic acid. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the remaining residue was purified by preparative HPLC chromatography (Method 21), which gave 4.5 mg (15% yield) of product.

Workup

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

Sources & evidence

ORD record
ord-620b36405d504f24945d749cf6fd12b2
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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