Sodium Hydroxide → HCID 136333918, compound

HRID 1409020Notes

Reaction equation

HRID 1409020 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([NH:10][C:11](=O)[CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:3]=1.[OH-].[Na+]>COCCOC>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:8])[NH:9][C:11]([CH:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71147160HCID 71147160, compound

Product 1

HCID 136333918HCID 136333918, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-3-{[phenyl(pyrrolidin-1-yl)acetyl]amino}thiophene-2-carboxamide (320 mg), 2M aqueous sodium hydroxide solution (3 mL) and 1,2-dimethoxyethane (1 mL) was stirred with heating in a microwave reactor at 150° C. for 30 min. The mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/hexane and methanol/ethyl acetate) to give the title compound (292 mg) as a pale-yellow solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/hexane and methanol/ethyl acetate)

Sources & evidence

ORD record
ord-67cf051f34174ab2a8306f784b7175e5
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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