HCID 12349168, compound → HCID 86725544, compound

HRID 514420Notes

Reaction equation

HRID 514420 reaction equation
C[N:2](C)/[CH:3]=[C:4](\[CH3:10])/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH:12]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][N:15]=1)N>CC(O)=O.CCO>[C:20]([C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:12][NH:2]/[CH:3]=[C:4](\[CH3:10])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:19]=1)#[N:21]

Participants

5

Reactant 2

HCID 12349168HCID 12349168, compoundHCID 201187142-Hydrazinylpyridine-4-carbonitrile

Product 1

HCID 86725544HCID 86725544, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of ethyl (E)-3-(dimethylamino)-2-methylprop-2-enoate (668 mg, 4.25 mmol) and 2-hydrazinylpyridine-4-carbonitrile (570 mg, 4.25 mmol, PREPARATION 2) in 2 mL HOAc and 10 mL EtOH was charged to a flask and the mixture was heated to 90° C. for 30 min. Cooled to room temperature and removed the solvent. The residue was dissolved in ethylacetate and water, aqueous basified with NaHCO3 sat (pH=8), extracted with ethylacetate. The organic phase was washed with brine and dried with anhydrous sodium sulfate and then purified by silica gel chromatograph to give 0.65 g of the title compound (62%). [M+H] Calc'd for C12H14N4O2, 247. Found, 247.

Workup

  1. temperatureCooled to room temperature
  2. customremoved the solvent
  3. dissolutionThe residue was dissolved in ethylacetate
  4. extractionextracted with ethylacetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. custompurified by silica gel chromatograph

Sources & evidence

ORD record
ord-9980974b9cc94381920fa24fa6f29915
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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