Hydrochloric Acid → HCID 22387864, compound

HRID 1072937Notes

Reaction equation

HRID 1072937 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]1([S:16]([NH:19][C:20]([C:22]2[N:27]=[C:26]3[N:28]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([CH2:39]OS(C)(=O)=O)=[CH:35][C:34]=4[Cl:45])[C:29]([CH3:31])=[N:30][C:25]3=[CH:24][CH:23]=2)=[O:21])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>CN(C)C=O.O>[C:10]1([S:16]([NH:19][C:20]([C:22]2[N:27]=[C:26]3[N:28]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([CH2:39][O:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:35][C:34]=4[Cl:45])[C:29]([CH3:31])=[N:30][C:25]3=[CH:24][CH:23]=2)=[O:21])(=[O:17])=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24758Sodium hydrideHCID 22388438HCID 22388438, compound

Product 1

HCID 22387864HCID 22387864, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of phenol (12 mg, 0.13 mmol) in N,N-dimethylformamide (0.5 ml) was added sodium hydride (60% in mineral oil, 5.2 mg) under ice-cooling. Thirty minutes later, a solution of 5-(benzenesulfonylcarbamoyl)-3-(2-chloro-4-((methanesulfonyloxy)methyl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (68 mg, 0.12 mmol) in N,N-dimethylformamide (1 ml) was dropwise added, which was followed by stirring at room temperature for 3 hr. The reaction mixture was cooled with ice and water was added. Its pH was adjusted to 4 by dropwise addition of 1N hydrochloric acid. The resulting product was extracted with ethyl acetate, washed three times with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel thin layer chromatography (eluent: chloroform/methanol=20/1) and crystallized from ethyl acetate to give 5-(benzenesulfonylcarbamoyl)-3-(2-chloro-4-((phenyloxy)methyl)-benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (30 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionThe resulting product was extracted with ethyl acetate
  4. washwashed three times with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fa5f7675924e4ab9b961fb0d0fae80b9
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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