Ethanol → 1-(2-(4-(5-Aminobenzo[b]thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 507535

반응식

HRID 507535 반응식
[Br:1][C:2]1[C:3]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][C:27]([N+:29]([O-])=O)=[CH:28][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1.C(O)C.[In]>O>[NH2:29][C:27]1[CH:26]=[CH:25][C:23]2[S:24][C:20]([C:3]3[C:2]([Br:1])=[CH:7][N:6]=[C:5]([NH:8][CH2:9][CH2:10][N:11]4[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]4=[O:19])[N:4]=3)=[CH:21][C:22]=2[CH:28]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 5359967IndiumHCID 602042651-(2-(5-Bromo-4-(5-nitrobenzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

생성물 1

HCID 116342761-(2-(4-(5-Aminobenzo[b]thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione수율 15.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 1-(2-(5-bromo-4-(5-nitrobenzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (996 mg, 1.97 mmol), ethanol (100 mL) and indium powder, 100 mesh (1.13 g, 9.85 mmol) was heated to reflux with stirring. After 1.5 h the reaction mixture was cooled to r.t., diluted with water (40 mL) and filtered through a pad of celite. The yellow precipitate (collected on the celite) was purified by reverse phase chromatography (0.1% TFA in AcCN:H20/10:90 to 95:5). The product fractions were combined, then passed through a 1 g SCX cartridge. The fully loaded cartridge was then washed with MeOH (4 mL) and 2 M ammonia in MeOH (8 mL). Elution of the desired compound was brought about by washing the cartridge finally with DMSO (4 mL). The solvent was removed in vacuo, employing a Genevac, to yield the title compound (142 mg, 15%) as a yellow amorphous solid. 1H NMR: δ (d6-DMSO, 400 MHz) 1.29 (s, 6H), 3.39-3.54 (m, 4H), 5.20 (s, 2H), 6.83 (d, J=8.61 Hz, 1H), 7.02 (s, 1H), 7.62 (d, J=8.61 Hz, 1H), 7.68 (s, 1H), 8.38 (s, 1H), 8.48 (s, 1H), 10.82 (s, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationfiltered through a pad of celite
  4. customThe yellow precipitate (collected on the celite)
  5. customwas purified by reverse phase chromatography (0.1% TFA in AcCN:H20/10:90 to 95:5)
  6. washThe fully loaded cartridge was then washed with MeOH (4 mL) and 2 M ammonia in MeOH (8 mL)
  7. washElution of the desired compound
  8. washby washing the cartridge finally with DMSO (4 mL)
  9. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-4a2e15363a9c49229102c0b4680b8ffe
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

연결된 노트

불러오는 중…