Guanidine → HCID 178432058, compound

HRID 1384295Notes

Reaction equation

HRID 1384295 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[Cl:5][CH:6]1[C:12]2=[N:13][C:14]([CH3:22])=[C:15]([C:17](OCC)=[O:18])[CH:16]=[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7]1>CC(O)C>[Cl:5][CH:6]1[C:12]2=[N:13][C:14]([CH3:22])=[C:15]([C:17]([NH:3][C:2]([NH2:4])=[NH:1])=[O:18])[CH:16]=[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 3520GuanidineHCID 21186666HCID 21186666, compound

Product 1

HCID 178432058HCID 178432058, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In an atmosphere of argon, guanidine hydrochloride (4.08 g, 42.7 mmol) was added to 28% sodium methoxide methanol solution (8.0 ml, 41.5 mmol) at 0° C. After 30 minutes of stirring at the same temperature, the thus precipitated sodium chloride was removed by filtration using a glass filter and the resulting filtrate was evaporated under reduced pressure to obtain free guanidine. Guanidine and ethyl 9-chloro-2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.10 g, 4.12 mmol) were suspended in 2-propanol (6.0 ml) and stirred at room temperature for 5 hours. The solvent was evaporated under reduced pressure, and the resulting residue was mixed with water and extracted with ethyl acetate. The thus obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1-5:1) to obtain the title compound (494.0 mg, 42.7%) as white powder.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe resulting residue was mixed with water
  3. extractionextracted with ethyl acetate
  4. washThe thus obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1-5:1)

Sources & evidence

ORD record
ord-1034cf12f9534fbc8a34cbd5cf0bcc76
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

Loading…