Trifluoroacetic acid → 4-[4-Carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidinium trifluoroacetate

HRID 521222Notes

Reaction equation

HRID 521222 reaction equation
[C:1]([C:4]1[C:5]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][N:7]([C:9]2([CH2:22][C:23]#[N:24])[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:8]=1)(=[O:3])[NH2:2].[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:32]([O-:38])=[O:33].[C:1]([C:4]1[C:5]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][N:7]([C:9]2([CH2:22][C:23]#[N:24])[CH2:14][CH2:13][NH2+:12][CH2:11][CH2:10]2)[CH:8]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71536247tert-Butyl 4-[4-carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidine-1-carboxylate

Product 1

HCID 867293834-[4-Carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidinium trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 4-[4-carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidine-1-carboxylate (2.0 g, 4.7 mmol) in DCM (20 mL) was added TFA (5.0 mL) dropwise. The resultant clear solution was maintained at ambient temperature for 1.5 hours. The mixture was then concentrated in vacuo, and the residue was dissolved in a mixture of MeCN/water (35 mL:15 mL) and lyophilized to afford the title compound, Example #38-1.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of MeCN/water (35 mL:15 mL)

Sources & evidence

ORD record
ord-62e21296db404c3cb0a66c10d5e0e97c
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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