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 2267420ノート

反応式

HRID 2267420 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-33ef8705095d43d29103e7f7aa594140
出典データセット
uspto-grants-2010_12
特許番号
US07858785B2

反応ノート

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