Ammonium Hydroxide → (+)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 840152Notes

Reaction equation

HRID 840152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[N:34]([CH3:38])[C:33](=[O:39])[CH:32]=[C:31]3[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([OH:27])[C:9]2[N:10]=[C:11]([Si](CC)(CC)CC)[N:12]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:13]=2)=[CH:4][CH:3]=1.[NH4+].[OH-]>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:28]2[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=2)[N:34]([CH3:38])[C:33](=[O:39])[CH:32]=[C:31]3[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([OH:27])[C:9]2[N:10]=[CH:11][N:12]([S:14]([N:17]([CH3:18])[CH3:19])(=[O:15])=[O:16])[CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 22714347(+/-)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-2-(triethylsilyl)-1H-imidazole-1-sulfonamide

Product 1

HCID 22714362(+)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamideYield 11.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of intermediate (3-a) (26 g) in sulfuric acid (2.5 ml) and water (250 ml) was stirred and heated at 110° C. for 2 hours. The mixture was poured into ice, basified with NH4OH and extracted with DCM. The organic layer was dried, filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.2). The pure fractions were collected and evaporated, yielding 2.4 g (11%) of (±)-4-[(4-chlorophenyl)(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)hydroxymethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide (interm. 3-b).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customevaporated till dryness
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 99/1/0.2)
  7. customThe pure fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-327af2661beb4787ba57c19c53054d4c
Source dataset
uspto-grants-2002_04
Patent number
US06365600B1

Reaction notes

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