4-Nitrobenzenesulfonyl chloride → HCID 22674107, compound

HRID 1173142Notes

Reaction equation

HRID 1173142 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 compound synthesized using 6-amino-1-methoxyisoquinoline (Production Example 43b) and 4-nitrobenzenesulfonyl chloride in the same manner as in Synthetic Example 1b was processed in the same manner as in Production Example 170b, to reduce the nitro group thereof. The resulting compound was dissolved in pyridine and methanesulfonyl chloride was added thereto under ice-cooling, followed by stirring for 4 hours as it was. Brine was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column and the resulting crystals were recrystallized from ethanol, to give the title compound.

Workup

  1. customThe compound synthesized
  2. temperatureunder ice-cooling
  3. extractionby extracting with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporating the solvent
  7. customthe residue was purified by silica gel column
  8. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-6832803b492d4221b50f476ba5b30a29
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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