Diethyl Ether → HCID 178512294, compound

HRID 1383450Notes

Reaction equation

HRID 1383450 reaction equation
CS[C:3](=[N:7][C:8]1C=CC=CN=1)[NH:4][C:5]#[N:6].[NH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.CCOCC>N1C=CC=CC=1>[C:5]([NH:4][C:3]([NH:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[N:7][C:8]1[CH:27]=[CH:26][N:25]=[CH:28][CH:29]=1)#[N:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 8795AminoethylpiperazineHCID 2761294HCID 2761294, compound

Product 1

HCID 178512294HCID 178512294, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

S-methyl-N-cyano-N′-pyridylisothiourea (3.84 g, 20 mmol) and 1-(2-aminoethyl)piperazine (2.89 ml, 22 mmol) were suspended in pyridine (8 mL) in a reaction flask equipped with magnetic stirring under nitrogen. Triethylamine (2.8 mL, 20 mmol) was added followed by (4-dimethylamino)-pyridine (cat., 100 mg). The reaction mixture became clear. It was stirred at 50-60° C. for 12 hours and cooled to room temperature. Ether (100 mL) was then added and precipitate formed. The precipitate was collected to give crude N-cyano-N′-(2-piperazin-1-yl-ethyl)-N″-pyridin-4-yl-guanidine which was used without further purification. ESMS 274.2 (M+1).

Workup

  1. customequipped
  2. stirringIt was stirred at 50-60° C. for 12 hours
  3. customprecipitate formed
  4. customThe precipitate was collected

Sources & evidence

ORD record
ord-e1418b90ec1249b49ba0959bb6a90164
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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