4-Nitrobenzenesulfonyl chloride → HCID 22674107, compound

HRID 1005699Notes

Reaction equation

HRID 1005699 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][CH3:13])=[N:7][CH:6]=[CH:5]2.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-])=O.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.[Cl-].[Na+].O>[CH3:27][S:28]([NH:14][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([O:12][CH3:13])=[N:7][CH:6]=[CH:5]3)(=[O:25])=[O:24])=[CH:19][CH:18]=1)(=[O:30])=[O:29]

Participants

6

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 31297Methanesulfonyl chlorideHCID 226740451-Methoxyisoquinolin-6-amine

Product 1

HCID 22674107HCID 22674107, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The nitro group of the compound synthesized in the same manner as in Example 1, except using 6-amino-1-methoxyisoquinoline (Preparation Example 43) and 4-nitrobenzenesulfonyl chloride was reduced in the same manner as in Preparation Example 170. The resulting compound was dissolved in pyridine, and under ice-cooling, methanesulfonyl chloride was added thereto, followed by stirring as it was for 4 hours. Brine was added thereto, followed by extracting with ethyl acetate, The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. Then, the residue was purified by silica gel column, and the resulting crystals were recrystallized from ethanol, to give the title compound.

Workup

  1. customThe nitro group of the compound synthesized in the same manner as in Example 1
  2. customwas reduced in the same manner as in Preparation Example 170
  3. temperatureunder ice-cooling
  4. extractionby extracting with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThen, the residue was purified by silica gel column
  9. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-7dab1240429149e88b968120772f4c55
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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