Isopropanol → (R)-N-[2-(Dimethylamino)-3-pyridyl]-N"-cyano-N'-(1-phenylethyl)guanidine

HRID 1378441Notes

Reaction equation

HRID 1378441 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].[CH3:22][C@@H:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN1CCOCC1.C(O)(C)C>CO>[CH3:14][N:12]([CH3:13])[C:7]1[C:6]([NH:5][C:4]([NH:30][C@@H:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:22])=[N:3][C:1]#[N:2])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 79724-MethylmorpholineHCID 6431891-Phenethylamine, (+)-HCID 178483039N'-Cyano-N-(2-dimethylamino-3-pyridyl)-O-phenylisourea

Product 1

HCID 178462037(R)-N-[2-(Dimethylamino)-3-pyridyl]-N"-cyano-N'-(1-phenylethyl)guanidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of the crude product from Step 3, (R)-(+)-α-methylbenzylamine (1.01 ml, 0.00782 mol), N-methylmorpholine (1.69 ml, 0.0154 mol) and isopropanol (20 ml) was refluxed, under nitrogen for 5 hours and then concentrated. The residue was chromatographed on silica gel first with mixtures of MeOH--CHCl3 containing from 1-10% MeOH to give an impure product which was rechromatographed on silica gel with mixtures of EtOAc-hexane containing from 1-50% EtOAc. The product obtained in this manner was dissolved in MeOH, decolorized with activated carbon and crystallized from MeOH-EtOAc-hexane to give 0.700 g of the titled product, mp 111°-128° C. (dec.).

Workup

  1. temperaturewas refluxed, under nitrogen for 5 hours
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel first with mixtures of MeOH
  4. customCHCl3 containing from 1-10% MeOH to give an impure product which
  5. customwas rechromatographed on silica gel with mixtures of EtOAc-hexane containing from 1-50% EtOAc
  6. customThe product obtained in this manner
  7. customcrystallized from MeOH-EtOAc-hexane

Sources & evidence

ORD record
ord-363fe3fcf24d4e5e975946916df74e9f
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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