4-Methylmorpholine → N-(5-Amino-6-chloro-3-pyridyl)-N"-cyano-N'-(1-phenylcyclobutyl)guanidine

HRID 1378433Notes

Reaction equation

HRID 1378433 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[N:18][C:19]#[N:20])OC2C=CC=CC=2)[CH:5]=[N:6][C:7]=1[Cl:8].[C:21]1([C:27]2([NH2:31])[CH2:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN1CCOCC1>O1CCOCC1>[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:31][C:27]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29][CH2:30]2)=[N:18][C:19]#[N:20])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1522141-PhenylcyclobutylamineHCID 178512301N-(5-Amino-6-chloro-3-pyridyl)-N'-cyano-O-phenylisourea

Product 1

HCID 178512300N-(5-Amino-6-chloro-3-pyridyl)-N"-cyano-N'-(1-phenylcyclobutyl)guanidineYield 34.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of the product from Step 2 (1.5 g, 0.0052 mol), 1-phenylcyclobutylamine (0.8 g, 0.00543 mol), N-methylmorpholine (1.37 ml, 0.0125 mol) and dioxane (30 ml) was refluxed, under nitrogen for 5 hours, cooled and filtered. The solid was washed with cold dioxane and Et2O and crystallized from acetonitrile to give 0.605 g of the titled product, mp 220°-221° C.

Workup

  1. temperaturewas refluxed, under nitrogen for 5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe solid was washed with cold dioxane and Et2O
  5. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-d6146df775264d1291c5adb2369fb4c5
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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