Acetohydrazide → HCID 178493714, compound

HRID 1394452Notes

Reaction equation

HRID 1394452 reaction equation
COC1C=[N:10][C:9]([C:12]#[N:13])=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15].[CH2:19]([O:21][C:22]([CH3:24])=O)C.O>>[CH3:19][O:21][C:22]1[CH:24]=[N:10][C:9]([C:12]2[NH:13][C:14]([CH3:15])=[N:17][N:18]=2)=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2

Participants

4

Reactant 3

HCID 14039AcetohydrazideHCID 22728543Water ethylacetateHCID 450911364-Methoxy-1H-pyrrolo[2,3-c]pyridine-7-carbonitrile

Product 1

HCID 178493714HCID 178493714, compoundYield 26%

Conditions

Temperature
150 °C

Procedure

A mixture of 4-methoxy-7-cyano-6-azaindole (0.131 g, 0.757 mmol) and acetic hydrazide (0.270 g, 3.645 mmol) was heated in a sealed tube at 150° C. for 48 h. The reaction mixture was cooled and the solid residue was diluted with EtOAc-H2O. The aqueous phase was separated and re-extracted twice with EtOAc. The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated, and the residue was purified by preparative HPLC (NH4OAc), affording the title compound (0.0455 g, 26%) as a colorless solid:

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe aqueous phase was separated
  3. extractionre-extracted twice with EtOAc
  4. washThe combined organic layers were washed (H2O, brine)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was purified by preparative HPLC (NH4OAc)

Sources & evidence

ORD record
ord-33af9e05e1614e2bb65af96c497fe89a
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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