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

HRID 1486356Notes

Reaction equation

HRID 1486356 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]([CH3:46])([CH2:43][CH2:44][CH3:45])[CH2:16][NH:17][C:18]([C:20]1[C:21]([CH3:42])=[N:22][N:23]2[C:28]([O:29][CH2:30][C:31]3[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=3[F:38])=[CH:27][C:26]([CH:39]3[CH2:41][CH2:40]3)=[CH:25][C:24]=12)=[O:19])(C)(C)C>ClCCl>[NH2:14][C:15]([CH3:46])([CH2:43][CH2:44][CH3:45])[CH2:16][NH:17][C:18]([C:20]1[C:21]([CH3:42])=[N:22][N:23]2[C:28]([O:29][CH2:30][C:31]3[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=3[F:38])=[CH:27][C:26]([CH:39]3[CH2:41][CH2:40]3)=[CH:25][C:24]=12)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117864545rac-{1-[({5-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

Product 1

HCID 117864719rac-N-(2-Amino-2-methylpentyl)-5-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of trifluoroacetic acid were added to a solution of 125 mg (0.2 mmol) of rac-{1-[({5-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic acid tert-butyl ester (Example 150A) in 4 ml of dichloromethane. The reaction mixture was stirred at room temperature for 1 h and concentrated under reduced pressure. The residue was purified by chromatography on SCX-2 silica gel (mobile phase: methanol then 20% (2 M ammonia in methanol) in dichloromethane). This gave 40 mg of the target compound (39% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography on SCX-2 silica gel (mobile phase

Sources & evidence

ORD record
ord-3379511f4ad44325a7c853da0d92110b
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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