Trifluoroacetic acid → Trifluoroacetate

HRID 2220140Notes

Reaction equation

HRID 2220140 reaction equation
C(OC([N:8]([C:18]1[N:23]2[N:24]=[CH:25][CH:26]=[C:22]2[C:21]([C:27]#[N:28])=[C:20]([NH:29][C@H:30]2[CH2:35][CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]2)[C:19]=1[CH3:43])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=O)(C)(C)C.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>ClCCl>[NH:32]1[CH2:33][CH2:34][CH2:35][C@H:30]([NH:29][C:20]2[C:19]([CH3:43])=[C:18]([NH:8][C:9]3[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=3)[N:23]3[N:24]=[CH:25][CH:26]=[C:22]3[C:21]=2[C:27]#[N:28])[CH2:31]1.[F:44][C:45]([F:50])([F:49])[C:46]([O-:48])=[O:47]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58837528HCID 58837528, compound

Product 2

HCID 84468TrifluoroacetateYield 24%HCID 11852873HCID 11852873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude product of tert-butyl (3S)-3-{7-[N-tert-butoxycarbonyl-N-(4-ethoxyphenyl)amino]-4-cyano-6-methylpyrazolo[1,5-a]pyridin-5-ylamino}piperidinecarboxylate (45) (6.1 mg) was dissolved in dichloromethane (350 μL). To this solution, trifluoroacetic acid (150 μL) was added and the mixture was stirred at room temperature for 1 h. The solvent and trifluoroacetic acid were removed under reduced pressure and the residue was purified with preparative HPLC to obtain the title compound (85) as trifluoroacetate salt (1.81 mg, Yield 24%).

Workup

  1. customThe solvent and trifluoroacetic acid were removed under reduced pressure
  2. customthe residue was purified with preparative HPLC

Sources & evidence

ORD record
ord-4dfbf5a7422a4c56b65047e9919ba2b3
Source dataset
uspto-grants-2008_08
Patent number
US07417053B2

Reaction notes

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