Methanesulfonic Acid → 9-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one methanesulfonate

HRID 1531017Notes

Reaction equation

HRID 1531017 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:20](=[O:30])[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)=[CH:22][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=3.[CH3:31][S:32]([OH:35])(=[O:34])=[O:33]>CO>[CH3:31][S:32]([OH:35])(=[O:34])=[O:33].[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:20](=[O:30])[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)=[CH:22][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=3

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 98724899-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 98724889-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one methanesulfonateYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

9-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (250 mg) obtained in Example 110 was suspended in methanol (200 ml) and to the suspension was added a solution of methanesulfonic acid (57 mg) in methanol (5 ml) at room temperature. The mixture was stirred for 30 minutes. The solvent was evaporated under reduced pressure, and the resulting crude crystals were washed with a small amount of methanol and ether in succession to obtain the title compound (270 mg, 89%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe resulting crude crystals were washed with a small amount of methanol and ether in succession

Sources & evidence

ORD record
ord-c730adfd030c422d9768f55f02bf3a77
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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