Trifluoroacetic acid → 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl)-N-isobutylcyclobut-2-enecarboxamide trifluoroacetate salt

HRID 1694411Notes

Reaction equation

HRID 1694411 reaction equation
[CH2:1]([NH:5][C:6]([CH:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:15]([F:25])[CH:14]=2)(O)[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3].[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>ClCCCl>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[F:25][C:15]1[CH:14]=[C:13]([C:10]2[CH2:11][CH:8]([C:6]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH:9]=2)[CH:18]=[CH:17][C:16]=1[CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 566482293-(3-Fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid isobutyl-amide

Product 1

HCID 866198543-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl)-N-isobutylcyclobut-2-enecarboxamide trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of Example 20, 3-(3-Fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid isobutyl-amide (3.71 g, 10.64 mmol) in trifluoroacetic acid (20 mL) and 1,2-dichloroethane (120 mL) was refluxed for 21 h and concentrated to give 8.6 g of crude 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl)-N-isobutylcyclobut-2-enecarboxamide trifluoroacetate salt and residual TFA as a dark red-brown oil. Diagnostic 1H NMR signals: (CDCl3) δ 7.48 (t, J=7.7 Hz, 1H), 7.23 (d, partially obscured by CHCl3 signal, 1H), 7.09 (dd, J=10.3, 1.5 Hz, 1H), 6.38 (d J=0.8 Hz, 1H), 4.33 (d, J=5.0 Hz, 1H), 3.77 (br s, 2H), 3.68 (d, J=4.6 Hz, 1H), 3.20-3.07 (m, 3 h), 2.98 (br s, 2H), 2.83 (dd, J=13.3, 1.7 Hz, 1H), 2.19-2.07 (m, 4H), 0.90 (d, J=7.1H, 6H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-e6267ad80a7d464fa598647de9147df4
Source dataset
uspto-grants-2012_04
Patent number
US08158673B2

Reaction notes

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