Hydrochloric Acid → HCID 67041730, compound

HRID 1405476Notes

Reaction equation

HRID 1405476 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:19][C:20]4[C:25]([N:26]=3)=[CH:24][C:23]([C:27]([O:29]C)=[O:28])=[CH:22][CH:21]=4)[CH2:13][CH2:12]2)[N:2]=1.[OH-].[Na+].Cl>CO.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:18]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[N:19][C:20]4[C:25]([N:26]=3)=[CH:24][C:23]([C:27]([OH:29])=[O:28])=[CH:22][CH:21]=4)[CH2:13][CH2:12]2)[N:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67041972HCID 67041972, compound

Product 1

HCID 67041730HCID 67041730, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-(isoquinolin-3-yl)piperazin-1-yl)-2-phenylquinoxaline-6-carboxylate (216.6 mg, 0.46 mmol, 1.00 equiv) in methanol (15 mL). This was followed by the addition of a solution of sodium hydroxide (91.2 mg, 2.28 mmol, 5.00 equiv) in water (2 mL), which was added dropwise with stirring. The resulting solution was stirred overnight at 50° C. in an oil bath. The pH value of the solution was adjusted to 3-4 with 1N hydrochloric acid. The resulting mixture was concentrated under vacuum. The resulting mixture was washed with methanol. This resulted in 56 mg (26%) of 3-(4-(isoquinolin-3-yl)piperazin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. additionwas added dropwise
  3. stirringThe resulting solution was stirred overnight at 50° C. in an oil bath
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. washThe resulting mixture was washed with methanol
  6. customThis resulted in 56 mg (26%) of 3-(4-(isoquinolin-3-yl)piperazin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-e32a5281ce8148029dd7fa4e71e38b1d
Source dataset
uspto-grants-2014_12
Patent number
US08916560B2

Reaction notes

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