Sodium Hydroxide → 2-Chloro-5-{[4-(5-chloro-isoquinolin-6-yloxy)-cyclohexylamino]-methyl}-benzenesulfonamide

HRID 2370733Notes

Reaction equation

HRID 2370733 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C@H:10]2[CH2:15][CH2:14][C@@H:13]([O:16][C:17]3[C:18]([Cl:27])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH:23]=[N:22][CH:21]=[CH:20]4)[CH2:12][CH2:11]2)=[CH:4][C:3]=1[S:28]([N:31]=CN(C)C)(=[O:30])=[O:29].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[C:18]([Cl:27])=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH:23]=[N:22][CH:21]=[CH:20]4)[CH2:12][CH2:11]2)=[CH:4][C:3]=1[S:28]([NH2:31])(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178484402HCID 178484402, compound

Product 1

HCID 592685782-Chloro-5-{[4-(5-chloro-isoquinolin-6-yloxy)-cyclohexylamino]-methyl}-benzenesulfonamideYield 48.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

53 mg 2-Chloro-5-{cis-[4-(5-chloro-isoquinolin-6-yloxy)-cyclohexylamino]-methyl}-N-dimethylaminomethylene-benzenesulfonamide (74) were dissolved in 5 ml ethanol. 2 ml 2N NaOH were added and the mixture was heated to 65° C. After 5 h, the solvent was removed i. vac., the residue was dissolved in H2O and neutralized by adding 1 N HCl. The precipitate was filtered and dried, to yield 23 mg of the title compound as hydrochloride. Rt=0.89 min (Method #1). Detected mass: 480.2/484.2 (M+H+).

Workup

  1. customthe solvent was removed i
  2. dissolution, the residue was dissolved in H2O
  3. additionby adding 1 N HCl
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-842c5f9ebf834beb925b663031b05a08
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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