Triethylamine → HCID 11553198, compound

HRID 1350856Notes

Reaction equation

HRID 1350856 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[C:21]([CH3:30])[CH:20]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[C:21]([CH3:30])[CH:20]=2)=[O:13])=[CH:14][CH:15]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 21097529N-[4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride

Product 1

HCID 11553198HCID 11553198, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a N,N-dimethylformamide (DMF) (15 ml) solution of (4-tert-butylphenoxy)acetic acid (312 mg, 1.50 mmol) and N-[4-(aminomethyl)-2-methylphenyl]methanesulfonamide hydrochloride (451 mg, 1.80 mmol), 1-ethyl-3-(3′-dimethylaminopr6pyl)carbodiimide hydrochloride (EDC) (518 mg, 2.70 mmol), 4-(dimethylamino)pyridine (DMAP) (55 mg, 0.45 mmol) and triethylamine (607mg, 6.0 mmol) were added and the mixture was stirred for 15 hours at ambient temperature. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with methylene dichloride. The organic layer was then washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to an amino bound silica gel chromatography column and eluted with methylene dichloride/methanol=100/1 to furnish 350 mg (58% yield) of the title compound as a white solid.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate
  2. extractioncrude products were extracted with methylene dichloride
  3. washThe organic layer was then washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customto separate solvent and sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto give a residue, which
  9. washeluted with methylene dichloride/methanol=100/1

Sources & evidence

ORD record
ord-6f7352a58c7e4daabb4a97f6a668842e
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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