Isopropylamine → N-[2-(5-Amino-4-isopropyl-4H-[1,2,4]triazol-3-yl)-4-chloro-phenyl]-4-tert-butyl-benzenesulfonamide

HRID 2094215ノート

反応式

HRID 2094215 の反応式
[N:1]#[C:2]Br.[C:4]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[C:19]([C:25]([NH:27][NH2:28])=O)=N[C:21]([Cl:24])=[CH:22][CH:23]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].[C:29](=O)([O-])[O-].[K+].[K+].[CH:35]([NH2:38])([CH3:37])[CH3:36]>O1CCOCC1.C(O)(=O)C>[NH2:1][C:2]1[N:38]([CH:35]([CH3:37])[CH3:36])[C:25]([C:19]2[CH:29]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=2[NH:17][S:14]([C:11]2[CH:10]=[CH:9][C:8]([C:4]([CH3:5])([CH3:6])[CH3:7])=[CH:13][CH:12]=2)(=[O:16])=[O:15])=[N:27][N:28]=1

参加物

7

反応物 4

HCID 6363IsopropylamineHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 866183534-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide

生成物 1

HCID 59302968N-[2-(5-Amino-4-isopropyl-4H-[1,2,4]triazol-3-yl)-4-chloro-phenyl]-4-tert-butyl-benzenesulfonamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

Cyanogen bromide (110.9 mg, 1.05 mmol) was added to a solution of 4-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide (200 mg, 0.524 mmol) and potassium carbonate (145 mg, 1.05 mmol) in dioxane (2 mL). The resultant mixture reaction was stirred for 18 h at room temperature. Isopropyl amine (0.18 mL, 2.09 mmol) and acetic acid (0.15 mL) were subsequently added and the reaction was heated at 135° C. for 18 h. The crude mixture was partitioned between ethyl acetate and water and the layers were separated. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine; dried over magnesium sulfate, and concentrated in vacuo. The crude product was subsequently purified via flash column chromatography (10-100% ethyl acetate and hexane) followed by preparative HPLC (10-90% gradient of MeCN-water) to afford the title compound as a white solid: MS (ES) M+H expected 449.1. found 449.2.

後処理

  1. temperaturethe reaction was heated at 135° C. for 18 h
  2. customThe crude mixture was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was subsequently purified via flash column chromatography (10-100% ethyl acetate and hexane)

出典と根拠

ORDレコード
ord-8ad9eeae150841bc809010fa191d5ea4
出典データセット
uspto-grants-2013_05
特許番号
US08445518B2

反応ノート

読み込み中…