Triethylamine → 4-(Pyridin-3-ylsulfamoylmethyl)benzoic Acid Methyl Ester

HRID 1727261Notes

Reaction equation

HRID 1727261 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11](Cl)(=[O:13])=[O:12])=[CH:6][CH:5]=1.[NH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11](=[O:13])(=[O:12])[NH:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 21804301Methyl 4-[(chlorosulfonyl)methyl]benzoate

Product 1

HCID 303913014-(Pyridin-3-ylsulfamoylmethyl)benzoic Acid Methyl EsterYield 81%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chlorosulfonylmethylbenzoic acid methyl ester (435 mg, 1.75 mmol) and 3-aminopyridine (170 mg, 1.81 mmol) in CH2Cl2 (10 mL) at 0° C. was added triethylamine (488 μL, 3.50 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with CHCl3, and the mixture was washed with water and brine. The organic layer was dried (Na2SO4) and evaporated under reduced pressure to give the crude product which was purified by MPLC on silica gel (3% MeOH in EtOAc) to afford the titled compound (434 mg, 81%) as a white solid.

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customto give the crude product which
  5. customwas purified by MPLC on silica gel (3% MeOH in EtOAc)

Sources & evidence

ORD record
ord-4375fbc633ca40edbdfe4b1fa0651bbc
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

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