Triethylamine → Methyl 5-[4-(ethylsulfonyl)phenoxy]-2-[(2-pyridinylcarbonyl)amino]benzoate

HRID 2080670Notes

Reaction equation

HRID 2080670 reaction equation
C(N(CC)CC)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](Cl)=[O:16].[NH2:18][C:19]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH2:39][CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:39]([S:36]([C:33]1[CH:32]=[CH:31][C:30]([O:29][C:26]2[CH:27]=[CH:28][C:19]([NH:18][C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=3)=[O:16])=[C:20]([CH:25]=2)[C:21]([O:23][CH3:24])=[O:22])=[CH:35][CH:34]=1)(=[O:38])=[O:37])[CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 516892Sodium BicarbonateHCID 57433574Methyl 2-amino-5-[4-(ethylsulfonyl)phenoxy]benzoate

Product 1

HCID 67110490Methyl 5-[4-(ethylsulfonyl)phenoxy]-2-[(2-pyridinylcarbonyl)amino]benzoateYield 54.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

With cooling with ice, 4.4 ml of triethylamine and 2.8 g of picolinic acid chloride hydrochloride were added to a chloroform (30 ml) solution of 2.65 g of methyl 2-amino-5-[4-(ethylsulfonyl)phenoxy]benzoate, and stirred at room temperature for 90 minutes. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, extracted with chloroform, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1) to obtain 1.9 g of the entitled compound as a creamy white solid.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline water
  3. customAfter dried
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-97aef66e9ebc4976b222451da946b012
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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