2-Methoxyethylamine → 3-Bromo-4-(2-methoxy-ethylamino)-5-(pyrrolidine-1-sulfonyl)-benzoic acid

HRID 909394Notes

Reaction equation

HRID 909394 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[C:10]=1F)[C:5]([OH:7])=[O:6].[CH3:20][O:21][CH2:22][CH2:23][NH2:24]>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[C:10]=1[NH:24][CH2:23][CH2:22][O:21][CH3:20])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 674126533-Bromo-4-fluoro-5-(pyrrolidine-1-sulfonyl)-benzoic acid

Product 1

HCID 674100903-Bromo-4-(2-methoxy-ethylamino)-5-(pyrrolidine-1-sulfonyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-Bromo-4-fluoro-5-(pyrrolidine-1-sulfonyl)-benzoic acid (500 mg) in 2-methoxy-ethylamine was heated at 80° C. for 3 h. The mixture was dissolved in 2 M aq. NaOH and washed with EtOAc. The aqueous layer was acidified with 2 M HCl and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated in vacuo. Yield: 543 mg.

Workup

  1. washwashed with EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1f40565bac84f6584eb21939d099775
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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