(+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedione → (+/-)-1-[3-[[(2,3-Dihydro-1,4-dioxino-[2,3-b]pyridin-3-yl)methyl](phenylmethyl)amino]-2-hydroxypropyl]-2,4-imidazolidine-dione

HRID 30092

Reaction equation

HRID 30092 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][CH:10]2[O:19][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[O:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:20]1[CH2:22][CH:21]1[CH2:23][N:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30]>CO>[O:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[O:19][CH:10]([CH2:9][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:22][CH:21]([OH:20])[CH2:23][N:24]2[CH2:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])[CH2:11]1

Participants

4

Reactant 2

HCID 22020929(+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedioneHCID 220209302,3-dihydro-N-(phenylmethyl)-1,4-dioxino[2,3-b]pyridine-3-methanamine

Product 1

HCID 22020928(+/-)-1-[3-[[(2,3-Dihydro-1,4-dioxino-[2,3-b]pyridin-3-yl)methyl](phenylmethyl)amino]-2-hydroxypropyl]-2,4-imidazolidine-dioneYield 62.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3-dihydro-N-(phenylmethyl)-1,4-dioxino[2,3-b]pyridine-3-methanamine (0.0059 mol) and intermediate (18) (0.00497 mol) in methanol (30 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/2-propanone 96/4, 90/10 and 80/20), then CH2Cl2/CH3OH 96/4 and 90/10). The product fractions were collected and the solvent was evaporated, yielding 1.29 g of (±)-1-[3-[[(2,3-dihydro-1,4-dioxino-[2,3-b]pyridin-3-yl)methyl](phenylmethyl)amino]-2-hydroxypropyl]-2,4-imidazolidine-dione (compound 12).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/2-propanone 96/4, 90/10 and 80/20)
  4. customThe product fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0eef55918a5646fd87a8980242071fb0
Source dataset
uspto-grants-2008_09
Patent number
US07423048B2

Linked notes

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