Sodium Hydroxide → HCID 17981877, compound

HRID 2252075Notes

Reaction equation

HRID 2252075 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:20]([CH:21]4[CH2:26][CH2:25][N:24](C(OCC)=O)[CH2:23][CH2:22]4)[CH:19]=[N:18][C:17]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:38])(=[O:6])=[O:5])([CH3:3])[CH3:2].[OH-].[Na+]>Cl>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:20]([CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[CH:19]=[N:18][C:17]=3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:38])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17981622HCID 17981622, compound

Product 1

HCID 17981877HCID 17981877, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Heat a mixture of 1-isopropylsulfonyl-2-amino-6-(1-(1-(ethoxycarbonyl)piperidin-4-yl)-4(phenyl)-imidazol-5-yl)benzimidazole (55 mg) in concentrated hydrochloric acid at reflux for 24 hours. Cool the mixture to room temperature, add 5 N sodium hydroxide until the mixture is basic, and extract with dichloromethane. Concentrate the organic phase under reduced pressure and subject the residue to silica gel chromatography, eluting with dichloromethane followed by 1:1 dichloromethane:methanol to provide 20 mg (43%) of the title compound. MS(ES+): m/z=465.0 (M+H)+

Workup

  1. temperatureHeat
  2. temperatureat reflux for 24 hours
  3. extractionextract with dichloromethane
  4. concentrationConcentrate the organic phase under reduced pressure
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-673aa68023ad4ad387d54e2fc5d5a256
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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