p-Toluenesulfonic acid monohydrate → HCID 10018012, compound

HRID 229728

Reaction equation

HRID 229728 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[NH:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[CH2:6][C:5]=2[C:4](=[O:22])[CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[CH3:1][CH:2]1[CH2:11][C:10]2[N:9]=[N:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:6][C:5]=2[C:4](=[O:22])[CH2:3]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 42467327-Methyl-3-(3-(trifluoromethyl)phenyl)-1,4,6,7,8-pentahydrocinnolin-5-one

Product 1

HCID 10018012HCID 10018012, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a pyridine solution (1 mL) of 7-methyl-3-(3-trifluoromethylphenyl)-4,6,7,8-tetrahydro-1H-cinnolin-5-one (136.2 mg, 0.44 mmol) obtained in Example 65 was added p-toluenesulfonic acid hydrate (84 mg, 0.44 mmol) and stirred at room temperature for 3 days. The reaction liquid was concentrated, followed by purification of residue obtained with silica gel column chromatography (methylene chloride/methanol=30/1) to obtain an objective compound (89.0 mg, 66.1%).

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. customfollowed by purification of residue
  4. customobtained with silica gel column chromatography (methylene chloride/methanol=30/1)

Sources & evidence

ORD record
ord-3d65f477759b46d29d8c9eeb51f701ee
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Linked notes

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