Methyl acetoacetate → HCID 68074134, compound

HRID 2363982Notes

Reaction equation

HRID 2363982 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[C:16]([O:22][CH3:23])(=[O:21])[CH2:17][C:18]([CH3:20])=O>CO.Cl>[CH3:20][C:18]1([CH2:17][C:16]([O:22][CH3:23])=[O:21])[NH:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=3)[S:4][C:3]=2[C:13](=[O:14])[NH:15]1

Participants

5

Reactant 2

HCID 7757Methyl acetoacetateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 68074134HCID 68074134, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.11 g, 0.50 mmol) and methyl acetoacetate (0.54 mL, 5.0 mmol) in methanol (15 mL) was added 1 drop of concentrated hydrochloric acid, and the reaction was heated at 55° C. for 15 h and with reflux for 24 h. Then, the reaction mixture was cooled, and concentrated with NaHCO3 (0.5 g) and silica gel (5 mL), and the residue was purified by flash chromatography (Combiflash, silica gel, dichloromethane to 90:10 dichloromethane/methanol) to give the title compound (0.075 g, 47%) as a yellow solid:

Workup

  1. temperaturewith reflux for 24 h
  2. temperatureThen, the reaction mixture was cooled
  3. concentrationconcentrated with NaHCO3 (0.5 g) and silica gel (5 mL)
  4. customthe residue was purified by flash chromatography (Combiflash, silica gel, dichloromethane to 90:10 dichloromethane/methanol)

Sources & evidence

ORD record
ord-9842754bffd54889943afb1b34bb190d
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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