(+/-)-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

반응식

HRID 30092 반응식
[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

참가 물질

4

반응물 2

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

생성물 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-dione수율 62.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0eef55918a5646fd87a8980242071fb0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423048B2

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