Hydrochloric Acid → HCID 178491630, compound

HRID 2289701Notes

Reaction equation

HRID 2289701 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([NH:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=3[O:28][CH3:29])[C:21]([O:23]C)=[O:22])(=[O:16])=[O:15])=[CH:11][CH:12]=2)[C:7]([NH:30][C:31]([NH2:33])=[NH:32])=[N:6][CH:5]=1.Cl>O1CCOCC1>[ClH:3].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([S:14]([NH:17][C:18]3[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=3[O:28][CH3:29])[C:21]([OH:23])=[O:22])(=[O:15])=[O:16])=[CH:11][CH:12]=2)[C:7]([NH:30][C:31]([NH2:33])=[NH:32])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178498287HCID 178498287, compound

Product 1

HCID 178491630HCID 178491630, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

An aqueous solution of NaOH (0.7 mL, 1.0 M, 0.7 mmol) was added slowly to a stirred solution of methyl 3-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}-4-methoxybenzoate (52.2 mg, 0.113 mmol) in dioxane (2.5 mL) and the mixture stirred at room temperature for 1.5 h, and then at 70° C. for 3 h. The mixture was cooled to room temperature, dilute HCl (2 mL, 2 N) was added, the solvents were evaporated in vacuo and the residue was dried by azeotroping with i-PrOH (×3). The solid was extracted with hot i-PrOH (×4), the combined organic extracts were filtered, and the solvents were evaporated in vacuo. The residue was triturated with Et2O to give 3-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}-4-methoxybenzoic acid hydrochloride (29 mg, 0.055 mmol) as a solid.

Workup

  1. waitat 70° C. for 3 h
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvents were evaporated in vacuo
  4. customthe residue was dried
  5. customby azeotroping with i-PrOH (×3)
  6. extractionThe solid was extracted with hot i-PrOH (×4)
  7. filtrationthe combined organic extracts were filtered
  8. customthe solvents were evaporated in vacuo
  9. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-d7663854f47d4295902d973faa0d5c46
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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