4-Methylmorpholine → N-[2-(Dimethylamino)-3-pyridyl]-N"-cyano-N'-(1-phenylcyclobutyl)guanidine

HRID 1378437Notes

Reaction equation

HRID 1378437 reaction equation
[C:1]([N:3]=[C:4](OC1C=CC=CC=1)[NH:5][C:6]1[C:7]([N:12]([CH3:14])[CH3:13])=[N:8][CH:9]=[CH:10][CH:11]=1)#[N:2].[C:22]1([C:28]2([NH2:32])[CH2:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN1CCOCC1>O1CCOCC1>[CH3:14][N:12]([CH3:13])[C:7]1[C:6]([NH:5][C:4]([NH:32][C:28]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:29][CH2:30][CH2:31]2)=[N:3][C:1]#[N:2])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1522141-PhenylcyclobutylamineHCID 178483039N'-Cyano-N-(2-dimethylamino-3-pyridyl)-O-phenylisourea

Product 1

HCID 178483038N-[2-(Dimethylamino)-3-pyridyl]-N"-cyano-N'-(1-phenylcyclobutyl)guanidineYield 44.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of the product from Step 1 (3.23 g, 0.0115 mol), 1-phenylcyclobutylamine (1.73 g, 0.0126 mol) (A. Kalir and Z. Pelah, Israel J. Chem. 5:223 (1967)), N-methylmorpholine (2.74 ml, 0.0249 mol) and dioxane (40 ml) was refluxed, under nitrogen for 18 hours and concentrated in vacuo. The residue was mixed with EtOAc and concentrated to give a solid which was recrystallized from EtOAc-hexane to give 1.7 g, mp 204°-205° C. of the titled product.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was mixed with EtOAc
  3. concentrationconcentrated
  4. customto give a solid which
  5. customwas recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-1f76135a2898439a9a2c7271201578d9
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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