HCID 667719, compound → HCID 15952363, compound

HRID 1924340Notes

Reaction equation

HRID 1924340 reaction equation
O[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[N:21]=2)[CH:18]=1>S(=O)(=O)(O)O.C(O)(=O)C.[Na]>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH2:2][N:3]3[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]3=[O:11])=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[N:21]=2)[CH:18]=1

Participants

6

Reactant 2

HCID 667719HCID 667719, compoundHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 15952363HCID 15952363, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent2×HCID 5360545SodiumSolvent

Procedure

To a refluxing solution of acetic acid (8 ml) and sulfuric acid (2 drops) is added, dropwised, a solution of 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (400 mg, 2.54 mmol) in 3 ml of acetic acid. 6-chloro-2-(4-methylphenyl)imidazo[1,2-a]pyridine x267 (309 mg, 1.27 mmol, 0.5 eq) is then added in once. The reaction mixture is refluxed for 3 days. After cooling, the reaction mixture is slowly poored in 150 ml of concentrated sodium hydroxyde solution (40% wt) and the crude product is extracted by dichloromethane (4×150 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under reduced pressure leading to the crude product which is purified by flash chromatography over silicagel (hexane/ethyl acetate 80/20). 1-{[6-chloro-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl}-4-propylpyrrolidin-2-one 4 is recrystallized in ethyl acetate.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 days
  2. temperatureAfter cooling
  3. extractionthe crude product is extracted by dichloromethane (4×150 ml)
  4. dry with materialThe cumulated organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customcondensed under reduced pressure
  7. customis purified by flash chromatography over silicagel (hexane/ethyl acetate 80/20)
  8. custom1-{[6-chloro-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methyl}-4-propylpyrrolidin-2-one 4 is recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-f7204a3d77fe433c9676739518767e8d
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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