Cyclohexylamine → 6-Chloro-4-(cyclohexylamino)pyridine-3-carboxyamide

HRID 2035527Notes

Reaction equation

HRID 2035527 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=[O:11].[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:8][C:6]1[N:5]=[CH:4][C:3]([CH2:9][C:10]([NH2:12])=[O:11])=[C:2]([NH:19][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 1317309314,6-Dichloropyridine-3-carboxyamide

Product 1

HCID 1317309936-Chloro-4-(cyclohexylamino)pyridine-3-carboxyamideYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 mg of 4,6-dichloropyridine-3-carboxyamide synthesized according to the method described in US2006/0217417 was dissolved in 2 mL of ethanol, to which 156 mg of cyclohexylamine and 203 mg of N,N-diisopropylethylamine were added, and heated at reflux for 8 hours. After cooling, the solvent was evaporated, and 10 mL of water was added to the residue, neutralized by adding 2 mol/L hydrochloric acid in water under ice cooling, extracted with chloroform, and the extract was dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was recrystallized from chloroform-hexane to obtain 243 mg (92%) of the title compound as colorless needle crystals.

Workup

  1. additionwere added
  2. temperatureheated
  3. temperatureat reflux for 8 hours
  4. temperatureAfter cooling
  5. customthe solvent was evaporated
  6. addition10 mL of water was added to the residue
  7. additionby adding 2 mol/L hydrochloric acid in water under ice cooling
  8. extractionextracted with chloroform
  9. dry with materialthe extract was dried on anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-21f32da1f4c741ab8524519e472ad27b
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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