Sodium Hydroxide → HCID 178519988, compound

HRID 352155Notes

Reaction equation

HRID 352155 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[N:19](COCC[Si](C)(C)C)[CH:20]=[C:21]([CH2:23][NH:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[N:22]=3)=[O:17])=[CH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:19][CH:20]=[C:21]([CH2:23][NH:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[N:22]=3)=[O:17])=[CH:8]2)=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22022394HCID 22022394, compound

Product 1

HCID 178519988HCID 178519988, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of [1-(4-chlorobenzyl)-1H-indol-3-yl]-[4-(pyridin-3-ylaminomethyl)-1-(2-trimethylsilanylethoxymethyl)-1H-imidazol-2-yl]methanone (43 mg, 7.52×10−5 mol) in ethanol (5 mL) and 2N HCl (5 mL) was heated to reflux for 2 h. The solution was allowed to cool to room temperature then neutralized with 2N NaOH. Solvent was removed under reduced pressure and ethyl acetate (50 mL) was added. The organic layer was washed with water, dried over MgSO4 and filtered. Solvent was removed under reduced pressure to produce a white powder (18 mg, 54%). 1H NMR; ESMS Calcd C25H20ClN5O 441.14, found: 442.2 (M+H)+.

Workup

  1. temperatureto reflux for 2 h
  2. customSolvent was removed under reduced pressure and ethyl acetate (50 mL)
  3. additionwas added
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d336e0a7f63940de9ea00089ff5fb473
Source dataset
uspto-grants-2004_06
Patent number
US06743919B2

Reaction notes

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