HCID 534555, compound → 5,5-Bis-pyridin-4-ylmethyl-2-thioxo-3-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-imidazolidin-4-one

HRID 1420786Notes

Reaction equation

HRID 1420786 reaction equation
CO[C:3](=[O:20])[C:4]([NH2:19])([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[CH3:21][CH:22]1[CH:27]2[C:28]([CH3:30])([CH3:29])[CH:25]([CH2:26]2)[CH2:24][CH:23]1[CH2:31][N:32]=[C:33]=[S:34]>C(O)C>[N:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:4]2([CH2:5][C:6]3[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=3)[NH:19][C:33](=[S:34])[N:32]([CH2:31][CH:23]3[CH2:24][CH:25]4[CH2:26][CH:27]([C:28]4([CH3:30])[CH3:29])[CH:22]3[CH3:21])[C:3]2=[O:20])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 534555HCID 534555, compoundHCID 15462778HCID 15462778, compound

Product 1

HCID 154627795,5-Bis-pyridin-4-ylmethyl-2-thioxo-3-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-imidazolidin-4-oneYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-Amino-3-pyridin-4-yl-2-pyridin-4-ylmethyl-propionic acid methyl ester (2.50 g, 9.23 mmol) was dissolved in absolute ethanol (50 ml). To the reaction was added 5.01 g (23.9 mmol) of (+)-3-pinanemethyl isothiocyanate. The reaction was then heated to 75° C. under an atmosphere of dry N2. After stirring for 16 hours, the reaction was subsequently concentrated under vacuum. The resulting oil was chromatographed on silica gel using a gradient of neat ethyl acetate to 5% methanol in ethyl acetate to give 3.32 g (7.41 mmol) of the titled compound.

Workup

  1. concentrationthe reaction was subsequently concentrated under vacuum
  2. customThe resulting oil was chromatographed on silica gel using a gradient of neat ethyl acetate to 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-744be6df361e4e97978db5a64717ccde
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

Loading…