Pyridine → HCID 136393923, compound

HRID 872109Notes

Reaction equation

HRID 872109 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.C[C:9]1[CH:10]=[C:11]([CH:15](C=O)[C:16](OC)=[O:17])C=CC=1.N1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:23][C:24]1[CH:9]=[C:10]([C:11]2[N:4]3[N:3]=[C:2]([CH3:1])[CH:6]=[C:5]3[NH:7][C:16](=[O:17])[CH:15]=2)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 86688010HCID 86688010, compoundHCID 178418690HCID 178418690, compound

Product 1

HCID 136393923HCID 136393923, compound

Procedure

3-Methylpyrazol-5-amine (431 mg) and methyl 3-methylphenyl-3-oxopropanoate (812 mg) are stirred overnight at 93° C. in a pyridine (10 mL) solvent. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield the target compound (673 mg).

Workup

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-849212a2194045c0899f5e7c737b42d9
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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