Water → HCID 60198400, compound

HRID 1403316Notes

Reaction equation

HRID 1403316 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:24]([N:25]([CH:27]([CH3:29])[CH3:28])[CH3:26])=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:30]([O:32]C)=[O:31])[CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[C:24]([N:25]([CH:27]([CH3:28])[CH3:29])[CH3:26])=[N:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:30]([OH:32])=[O:31])[CH:21]=3)[N:16]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 60171605HCID 60171605, compound

Product 1

HCID 60198400HCID 60198400, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(6-(tert-butoxycarbonylamino)pyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (160.0 mg, 0.35 mmol) in methanol (30 mL) was added sodium hydroxide (43.0 mg, 1.06 mmol) and water (1 mL). The reaction mixture was stirred overnight at room temperature and concentrated under vacuum. The residue was dissolved in water (30 mL) and adjusted to pH 6 with HCl (3N). The solids were collected, dried in an oven under reduced pressure to afford 2-(6-(tert-butoxycarbonylamino)pyridin-3-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (53.5 mg, 33%).

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. customThe solids were collected
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-236df52ce4c14e42a26924fed91f43b1
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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