Sodium Hydroxide → HCID 178474713, compound

HRID 1881488Notes

Reaction equation

HRID 1881488 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][C:4]1[N:5]=[C:6]([C:15](O)([CH3:30])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)=[CH:19][CH:18]=2)[N:7](S(N(C)C)(=O)=O)[CH:8]=1.[OH-:34].[Na+].S(=O)(=O)(O)O.[C:41](#[N:43])[CH3:42]>>[CH3:32][C:2]([CH3:33])([CH3:1])[CH2:3][C:4]1[N:5]=[C:6]([C:15]([NH:43][C:41](=[O:34])[CH3:42])([CH3:30])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)=[CH:19][CH:18]=2)[NH:7][CH:8]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 22284053Sulfuric acid acetonitrileHCID 667058194-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 178474713HCID 178474713, compound

Conditions

Temperature
140 °C

Procedure

4-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (for synthesis see Example 15) (20 mg, 0.042 mmol) was dissolved in sulfuric acid/acetonitrile (1:1) (2 mL). After stirring at 140° C. overnight, the reaction mixture was cooled to ambient temperature, neutralized with aqueous sodium hydroxide and extracted with chloroform. The combined organic extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo to afford the title compound. (M+H) found: 409.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1420fff4deb04013a300da8b9efa089b
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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