2-Acetylpyrrole → HCID 51353096, compound

HRID 1406692Notes

Reaction equation

HRID 1406692 reaction equation
[C:1]([C:4]1[NH:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]3[N:23]([C:24]=2[CH:25]=O)[CH:22]=[CH:21][S:20]3)=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C.CCCCCC>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[C:19]3[N:23]([C:24]=2/[CH:25]=[CH:2]/[C:1]([C:4]2[NH:5][CH:6]=[CH:7][CH:8]=2)=[O:3])[CH:22]=[CH:21][S:20]3)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 140792-AcetylpyrroleHCID 14798Sodium HydroxideHCID 1515983HCID 1515983, compound

Product 1

HCID 51353096HCID 51353096, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
27 °C

Procedure

To a stirred solution of 2-acetyl pyrrole (109 mg, 1.0 mmol) and a 6-(4-methoxyphenyl) imidazo[2,1-b]thiazol-5-carbaldehyde (258 mg, 1.0 mmol) in ethanol (20 ml) 10% aqueous solution of NaOH was added (5 ml). The reaction mixture was stirred at room temperature 27° C. for 4 h and the reaction was monitored by TLC using ethyl acetate-hexane (3:7) as a solvent system. The solvent was evaporated under vacuum then the residue was dissolved in ethylacetate/water. The organic layer was washed with brine and evaporated. This was further purified by column chromatography using ethyl acetate:hexane (2:8) as a solvent system to obtain the pure product (17a) as yellow solid (286 mg, 82% yield). Mp: 177-179° C.

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue was dissolved in ethylacetate/water
  3. washThe organic layer was washed with brine
  4. customevaporated
  5. customThis was further purified by column chromatography

Sources & evidence

ORD record
ord-98e8728efd5745b9aaffe17c38a49ba7
Source dataset
uspto-grants-2014_12
Patent number
US08916711B2

Reaction notes

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