Water → HCID 50991750, compound

HRID 1403330Notes

Reaction equation

HRID 1403330 reaction equation
[CH:1]1([N:4]([CH3:28])[C:5]2[C:6]([CH:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)C3)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1.[OH:29][Li].O.O>CO.C(Cl)(Cl)Cl>[O:29]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[CH:27]=[C:19]1[C:6]1[C:5]([N:4]([CH:1]2[CH2:3][CH2:2]2)[CH3:28])=[N:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=2)[N:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 70665381HCID 70665381, compound

Product 1

HCID 50991750HCID 50991750, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 3-(cyclopropyl(methyl)amino)-2-(2,3-dihydro-1H-inden-2-yl)quinoxaline-6-carboxylate (95.0 mg, 0.25 mmol) in methanol (15 mL) and CHCl3 (10 mL) was added LiOH.H2O (35.0 mg, 0.83 mmol) and water (1 mL). The resulting solution was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (10 mL) and adjusted pH to 6 with hydrochloric acid (1N). The solids were collected by filtration to afford 2-(benzofuran-2-yl)-3-(cyclopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a yellow solid (43.6 mg, 48%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (10 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-4c65255f143f40a9b470a53f2c122908
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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