Trifluoroacetic acid → HCID 68289121, compound

HRID 541206Notes

Reaction equation

HRID 541206 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2([F:22])[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)#[N:2].[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>ClCCl>[F:26][C:25]([F:28])([F:27])[C:23]([OH:29])=[O:24].[F:22][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68288303HCID 68288303, compound2×

Product 1

HCID 68289121HCID 68289121, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of tert-butyl 4-(5-cyanopyridin-2-yl)-4-fluoropiperidine-1-carboxylate (compound 26.3, 1 g, 3.11 mmol, 1.00 equiv, 95%) in dichloromethane (20 mL) was added dropwise TFA (3.75 g, 32.89 mmol, 10.57 equiv). After stirring for 1 h at 25° C., the mixture was concentrated under reduced pressure to yield 0.5 g of the title compound as a brown oil.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e58efbf7eed4f969696fab6bfe0fa6c
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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