Trifluoroacetic acid → HCID 59350838, compound

HRID 1644725Notes

Reaction equation

HRID 1644725 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH:39]=[O:40])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:38][C:36]1[CH:35]=[CH:34][C:33]([CH:39]=[O:40])=[C:32]([C:31]#[C:30][C:27]2[CH:26]=[CH:25][C:24]([S:21]([N:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)(=[O:23])=[O:22])=[CH:29][CH:28]=2)[CH:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59350842HCID 59350842, compound

Product 1

HCID 59350838HCID 59350838, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.18 mL, 15.87 mmol) was added to a stirred solution of 4-[4-(5-fluoro-2-formyl-phenylethynyl)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.500 g, 1.06 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred at room temperature for 4 hours, then concentrated under reduced pressure. The viscous liquid was washed with ether (3×5 mL) to obtain 0.310 g (60.2%) of 4-fluoro-2-[4-(piperazine-1-sulfonyl)-phenylethynyl]-benzaldehyde as a yellow solid. MS cald. for C19H17FN2O3S [(M+H)+] 373, obsd. 373.3.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe viscous liquid was washed with ether (3×5 mL)

Sources & evidence

ORD record
ord-ca42a9b8c74840e29a0d7d131e89449e
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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