Cyanamide → HCID 21704195, compound

HRID 1595202Notes

Reaction equation

HRID 1595202 reaction equation
C([O:9][CH:10]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[C:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=O)(=O)C1C=CC=CC=1.[N:26]#[C:27][NH2:28].[OH-].[K+]>CCO>[NH2:26][C:27]1[O:9][C:10]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[N:28]=1

Participants

5

Reactant 3

HCID 9864CyanamideHCID 14797Potassium HydroxideHCID 13812200HCID 13812200, compound

Product 1

HCID 21704195HCID 21704195, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(t-butyldimethylsilyloxy)-2-(4-fluorophenyl)-1-(4-pyridyl)ethanone [See Ex. 79 (a) of Adams et al., WO93/14081] (5.16 g, 15.0 mmol), cyanamide (0.95 g, 22.5 mmol) and KOH (0.55 g, 9.8 mmol) in EtOH (20 mL) was heated at reflux for 1 h. After cooling, the precipitate was filtered and washed with EtOH. Recrystallization from CH2Cl2/MeOH afforded the title compound as a yellow solid (0.38 g): ESMS (m/z): 256 (M++H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered
  5. washwashed with EtOH
  6. customRecrystallization from CH2Cl2/MeOH

Sources & evidence

ORD record
ord-b02e5c1ad0204334a43f1983e2ef3994
Source dataset
uspto-grants-2001_09
Patent number
US06288062B1

Reaction notes

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