Sodium Hydroxide → HCID 22485223, compound

HRID 1368254Notes

Reaction equation

HRID 1368254 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[CH:33]=[CH:32][C:19]([CH2:20][N:21]2[C:25]3=[N:26][C:27]([Br:30])=[CH:28][CH:29]=[C:24]3[N:23]=[C:22]2[CH3:31])=[C:18]([Cl:34])[CH:17]=1)C(OC(C)(C)C)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][C:16]1[CH:33]=[CH:32][C:19]([CH2:20][N:21]2[C:25]3=[N:26][C:27]([Br:30])=[CH:28][CH:29]=[C:24]3[N:23]=[C:22]2[CH3:31])=[C:18]([Cl:34])[CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22485082HCID 22485082, compound

Product 1

HCID 22485223HCID 22485223, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A crude product (1.90 g) of 3-(4-(N,N-bis-(tert-butoxycarbonyl)amino)-2-chlorobenzyl)-5-bromo-2-methyl-3H-imidazo[4,5-b]pyridine was dissolved in 1,4-dioxane (19 ml) and 1N aqueous sodium hydroxide solution (7.0 ml) was added, which was followed by refluxing under heating for 8 hr. The mixture was allowed to cool, neutralized and stirred at room temperature for 30 min. The precipitate was collected by filtration, and washed with water to give 3-(4-(N-(tert-butoxycarbonyl)amino)-2-chlorobenzyl)-5-bromo-2-methyl-3H-imidazo[4,5-b]pyridine (1.45 g) as a pale-gray powder.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 8 hr
  3. temperatureto cool
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-e3d3a1dab9294132a088c6bbb29f5f22
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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