Sodium Hydroxide → HCID 178438886, compound

HRID 1881517Notes

Reaction equation

HRID 1881517 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[CH2:3][C:4]1[N:5]=[C:6]([CH:15]([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-].[Na+]>Cl.C1COCC1>[CH3:1][C:2]([CH3:31])([CH3:32])[CH2:3][C:4]1[N:5]=[C:6]([CH:15]([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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 667056824-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 178438886HCID 178438886, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2,2-dimethylpropyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide in 1.5 N hydrochloric acid (1 mL) and THF (1 mL) was heated at 70° C. in a sealed tube overnight. The reaction mixture was basified with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. Purification of the resulting crude product by silica preparatory plate chromatography eluting with 10% methanol/ethyl acetate afforded the title compound. LCMS: (M+H) found 352.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (sodium sulfate)
  3. concentrationconcentrated in vacuo
  4. customPurification of the resulting crude product by silica preparatory plate chromatography
  5. washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-b1478d3b396248d784251a63b8861a60
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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