Sodium Bicarbonate → HCID 86600995, compound

HRID 1351304Notes

Reaction equation

HRID 1351304 reaction equation
[CH3:1][NH:2][CH3:3].O1CCCC1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([CH3:31])[S:19]([C:22]2[CH:26]=[C:25]([C:27](=[O:30])[CH2:28]Br)[S:24][CH:23]=2)(=[O:21])=[O:20])=[CH:12][CH:11]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([CH3:31])[S:19]([C:22]2[CH:26]=[C:25]([C:27](=[O:30])[CH2:28][N:2]([CH3:3])[CH3:1])[S:24][CH:23]=2)(=[O:21])=[O:20])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22320367Dimethylamine tetrahydrofuranHCID 86600996HCID 86600996, compound

Product 1

HCID 86600995HCID 86600995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (0.6 mL) of 2.0M dimethylamine-tetrahydrofuran diluted with tetrahydrofuran (2 mL), was added dropwise 5-(2-bromoacetyl)thiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amide (46 mg) in tetrahydrofuran (1 mL) at room temperature. An aqueous solution of saturated sodium bicarbonate was added, and the solution was extracted with ethyl acetate. After the organic layer was washed with saturated sodium chloride water and dried with anhydrous sodium sulfate, the residuals that were obtained upon removing the solvent by evaporation were purified by silica gel column chromatography (dichloromethane/methanol), and the title compound (16 mg) was obtained as a yellow oily substance.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washAfter the organic layer was washed with saturated sodium chloride water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customthe residuals that were obtained
  5. customupon removing the solvent
  6. customby evaporation
  7. customwere purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-5746199e44474ade8922a326aef9d7c9
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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