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

HRID 2267310

反応式

HRID 2267310 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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:H2O/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, 6 H), 3.39-3.54 (m, 4 H), 5.20 (s, 2 H), 6.83 (d, J=8.61 Hz, 1 H), 7.02 (s, 1 H), 7.62 (d, J=8.61 Hz, 1 H), 7.68 (s, 1 H), 8.38 (s, 1 H), 8.48 (s, 1 H), 10.82 (s, 1 H).

後処理

  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:H2O/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

出典と根拠

ORDレコード
ord-5238a6d21f3242d0a83005a53983c95e
出典データセット
uspto-grants-2010_12
特許番号
US07858785B2

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