Chloroform → HCID 22388393, compound

HRID 1072935Notes

Reaction equation

HRID 1072935 reaction equation
[C:1]1([S:7]([NH:10][C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[CH:26][C:25]=4[Cl:38])[C:20]([CH3:22])=[N:21][C:16]3=[CH:15][CH:14]=2)=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.O1CCOCC1>[Pt]=O.CO>[C:1]1([S:7]([NH:10][C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)=[CH:26][C:25]=4[Cl:38])[C:20]([CH3:22])=[N:21][C:16]3=[CH:15][CH:14]=2)=[O:12])(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 312751,4-DioxaneHCID 22388404HCID 22388404, compound

Product 1

HCID 22388393HCID 22388393, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

(E)-5-(Benzenesulfonylcarbamoyl)-3-(2-chloro-4-(2-phenylethenyl)-benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (42 mg) was suspended in a mixed solvent of chloroform (4 ml), 1,4-dioxane (2 ml) and methanol (2 ml), and platinum oxide (2 mg) was added. The mixture was stirred at room temperature for 6.5 hr under a hydrogen atmosphere at 1 atm. The reaction mixture was filtrated and the solvent was evaporated. The resultant mixture was purified by silica gel column chromatography (chloroform/methanol=20/1) and crystallized from ethyl acetate/hexane to give 5-(benzenesulfonylcarbamoyl)-3-(2-chloro-4-(2-phenylethyl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (18 mg) as a white powder.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtrated
  3. customthe solvent was evaporated
  4. customThe resultant mixture was purified by silica gel column chromatography (chloroform/methanol=20/1)
  5. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-aa0b2495d30749f4bae67b398f44f58e
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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