Trifluoroacetic acid → HCID 56648226, compound

HRID 1943269Notes

Reaction equation

HRID 1943269 reaction equation
[CH2:1]([N:3]([CH3:24])[C:4]([CH:6]1[CH2:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:13]([F:23])[CH:12]=2)(O)[CH2:7]1)=[O:5])[CH3:2].[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>ClCCCl>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH2:1]([N:3]([CH3:24])[C:4]([CH:6]1[CH2:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:13]([F:23])[CH:12]=2)=[CH:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56648225HCID 56648225, compound

Product 1

HCID 56648226HCID 56648226, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(3-Fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid ethyl-methyl-amide (Example 14, 35.15 g, 105.1 mmol) was dissolved in a mixture of 1,2-dichloroethane (1 L) and trifluoroacetic acid (150 mL) and refluxed for 16 h. The resulting dark brown solution was cooled and concentrated to yield a brown oil (94.46) of crude title compound, N-ethyl-3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl)-N-methylcyclobut-2-enecarboxamide trifluoroacetate salt, with residual TFA, which was used in the next step without purification.

Workup

  1. temperaturerefluxed for 16 h
  2. temperatureThe resulting dark brown solution was cooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5773f7b2f5a649599fa811733beac10f
Source dataset
uspto-grants-2013_03
Patent number
US08389743B2

Reaction notes

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