Water → phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone semicarbazone

HRID 1821860Notes

Reaction equation

HRID 1821860 reaction equation
[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][NH:20][C:21]([NH2:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[N:19][NH:20][C:21]([NH2:23])=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11236Semicarbazide hydrochlorideHCID 11430Potassium CarbonateHCID 57893467phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

Product 1

HCID 136386499phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone semicarbazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (108 mg, 0.49 mmol), semicarbazide hydrochloride (57 mg, 0.51 mmol) and potassium carbonate (58 mg, 0.42 mmol) in ethanol (3.0 mL) was refluxed under a nitrogen atmosphere overnight (14 h). The reaction mixture was cooled to room temperature, water was added, and the reaction mixture was extracted with EtOAc (2×). The combined organic extracts were dried over Na2SO4. After filtration and concentration, the crude material was purified by Biotage chromatography to afford phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone semicarbazone as two isomers, Example 62 (5.3 mg, 4%) and Example 63 (5.9 mg, 4%), as a yellow solid:

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere overnight (14 h)
  2. extractionthe reaction mixture was extracted with EtOAc (2×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude material was purified by Biotage chromatography

Sources & evidence

ORD record
ord-ec90fc8756eb4d3b87bf67741d018d3d
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

Loading…