Diisopropylethylamine → 1-(2-(5-Chloro-4-(5-(phenylamino)-1,3,4-thiadiazol-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione

HRID 507643ノート

反応式

HRID 507643 の反応式
[Cl:1][C:2]1[C:3]([C:10]2[S:14][C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=3)=[N:12][N:11]=2)=[N:4][C:5](SC)=[N:6][CH:7]=1.OOS([O-])=O.[K+].[NH2:29][CH2:30][CH2:31][N:32]1[C:36]([CH3:38])([CH3:37])[C:35](=[O:39])[NH:34][C:33]1=[O:40].C(N(C(C)C)CC)(C)C>CC(C)=O.O.CC(O)C>[Cl:1][C:2]1[C:3]([C:10]2[S:14][C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][N:11]=2)=[N:4][C:5]([NH:29][CH2:30][CH2:31][N:32]2[C:36]([CH3:37])([CH3:38])[C:35](=[O:39])[NH:34][C:33]2=[O:40])=[N:6][CH:7]=1

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 23707502Potassium hydroxy sulfiteHCID 574288041-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dioneHCID 602045505-(5-Chloro-2-(methylthio)pyrimidin-4-yl)-N-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine

生成物 1

HCID 602045481-(2-(5-Chloro-4-(5-(phenylamino)-1,3,4-thiadiazol-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione収率 69.9%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

5-(5-Chloro-2-(methylthio)pyrimidin-4-yl)-N-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine (0.637 g, 1.7 mmol) was dissolved in 300 mL acetone. Oxone (6.3 g, 10.3 mmol) was dissolved in 300 mL H2O and added in one portion to the acetone solution and allowed to stir overnight at room temperature. The acetone was removed under vacuum, the resulting precipitate was obtained by filtration. LC/MS analysis indicates a mixture of both sulfoxide and sulfone. This solid mixture was dried briefly in a vacuum oven. This material was charged to a microwave reaction vessel along with 1-(2-aminoethyl)-5,5-dimethyl-imidazolidine-2,4-dione (0.588 g, 3.4 mmol), diisopropyl ethylamine (0.60 mL, 3.4 mmol) and 15 mL IPA. This reaction was heated under microwave conditions to 170° C. for 1200 s. Upon cooling 0.545 g (67% yield) of product was obtained by filtration. MS (M+H)+ 477.

後処理

  1. customThe acetone was removed under vacuum
  2. customthe resulting precipitate was obtained by filtration
  3. customThis solid mixture was dried briefly in a vacuum oven
  4. temperatureThis reaction was heated under microwave conditions to 170° C. for 1200 s

出典と根拠

ORDレコード
ord-62ce5b20cb974b3aa80140349d3e8b47
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

読み込み中…