Sodium Hydroxide → HCID 70665098, compound

HRID 1403446Notes

Reaction equation

HRID 1403446 reaction equation
[CH3:1][N:2]([CH:30]([CH3:32])[CH3:31])[C:3]1[C:4]([C:17]2[C:21]3[CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=[CH:25][C:20]=3[O:19][CH:18]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=2.[OH-].[Na+]>CO.O>[CH3:1][N:2]([CH:30]([CH3:32])[CH3:31])[C:3]1[C:4]([C:17]2[C:21]3[CH:22]=[C:23]([C:26]([F:29])([F:27])[F:28])[CH:24]=[CH:25][C:20]=3[O:19][CH:18]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([OH:15])=[O:14])=[CH:8][CH:7]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70665349HCID 70665349, compound

Product 1

HCID 70665098HCID 70665098, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-[methyl(propan-2-yl)amino]-2-[5-(trifluoromethyl)-1-benzofuran-3-yl]quinoxaline-6-carboxylate (135 mg, 0.30 mmol) in methanol (30 mL) and water (1.0 mL) was added sodium hydroxide (48.8 mg, 1.22 mmol) with stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (20 mL) and adjusted to pH 5 with HCl (3N). The solids were collected by filtration to afford 3-[methyl(propan-2-yl)amino]-2-[5-(trifluoromethyl)-1-benzofuran-3-yl]quinoxaline-6-carboxylic acid as a light yellow solid (42.6 mg, 33%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (20 mL)
  3. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-d5e4dd8dbd6e4f20966ccd142ee675c0
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…