Water → HCID 70664745, compound

HRID 1403393Notes

Reaction equation

HRID 1403393 reaction equation
[N:1]1([C:8]2[C:9]([C:22]3[O:23][C:24]4[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:25]=4[CH:26]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O>CO.C(Cl)(Cl)Cl>[N:1]1([C:8]2[C:9]([C:22]3[O:23][C:24]4[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:25]=4[CH:26]=3)=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70654216HCID 70654216, compound

Product 1

HCID 70664745HCID 70664745, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 3-(azepan-1-yl)-2-(6-fluoro-1-benzofuran-2-yl)quinoxaline-6-carboxylate (73 mg, 0.17 mmol) in methanol (25 mL) and chloroform (5 mL) was added sodium hydroxide (13.6 mg, 0.34 mmol) and water (2 mL) with stirring overnight at room temperature. The reaction mixture was concentrated under vacuum, dissolved in water (15 mL), adjusted pH to 5 with HCl (3 N) to give the precipitate, which was collected by filtration to afford 3-(azepan-1-yl)-2-(6-fluoro-1-benzofuran-2-yl)quinoxaline-6-carboxylic acid (39 mg, 55%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in water (15 mL)
  3. customto give the precipitate, which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-bb1e7a3f13084034956e554c0b702727
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…