Potassium Carbonate → HCID 86702008, compound

HRID 717980Notes

Reaction equation

HRID 717980 reaction equation
[CH:1]1([C:4]#[C:5][C:6]([C:8]2[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=2)=O)[CH2:3][CH2:2]1.Cl.[CH2:18]([NH:25][NH2:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:18]([N:25]1[C:6]([C:8]2[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=2)=[CH:5][C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14084Hydrazine, (phenylmethyl)-, hydrochloride (1:1)HCID 86702007HCID 86702007, compound

Product 1

HCID 86702008HCID 86702008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 5-(3-cyclopropylpropioloyl)thiophene-2-carboxylate (100 mg, 0.427 mmol) was dissolved in N,N-dimethylformamide (2 mL), and the solution was cooled to 0° C. Benzylhydrazine hydrochloride (74.5 mg, 0.470 mmol) was added followed by potassium carbonate (77 mg, 0.555 mmol). The mixture was stirred at 0° C. until the ice bath melted and was stirred overnight at room temperature. The solution was partitioned between water and ethyl acetate. The organic extract was dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-fce876078c384025bb64a5b92df8c0a0
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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