Trifluoroacetic acid → 4-Cyano-3-(2,4-dichlorophenyl)-N-hydroxy-5-morpholin-4-yl-thiophene-2-carboxamide

HRID 572630Notes

Reaction equation

HRID 572630 reaction equation
[C:1]([C:3]1[C:4]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[C:5]([C:14]([NH:16][O:17]C2CCCCO2)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[C:5]([C:14]([NH:16][OH:17])=[O:15])[S:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866375484-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide

Product 1

HCID 441551214-Cyano-3-(2,4-dichlorophenyl)-N-hydroxy-5-morpholin-4-yl-thiophene-2-carboxamideYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide (0.050 g, 0.10 mmol) was dissolved in DCM (3 mL) and TFA (0.24 mL, 3.11 mmol) was added. The solution was stirred at room temperature overnight. Solvent was evaporated and the residue was purified by column chromatography (silica gel, elution with DCM to 10% MeOH in DCM over 20 minutes) to give the title compound 24 (0.030 g, 67%). LCMS: (FA) ES+ 398.

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by column chromatography (silica gel, elution with DCM to 10% MeOH in DCM over 20 minutes)

Sources & evidence

ORD record
ord-784169b2c59e459d81516dd34ad282bc
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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