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

HRID 1692132ノート

反応式

HRID 1692132 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[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[C:25]([NH:27][NH2:28])=O)(=[O:16])=[O:15])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].C(=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:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=2[NH:17][S:14]([C:11]2[CH:12]=[CH:13][C:8]([C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:9][CH:10]=2)(=[O:16])=[O:15])=[N:27][N:28]=1

参加物

7

反応物 4

HCID 6363IsopropylamineHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 593029884-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)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 (111 mg, 1.05 mmol) was added to a solution of 4-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (200 mg, 0.524 mmol) and potassium carbonate (145 mg, 1.05 mmol) in dioxane (2 mL) and the reaction was stirred for 18 h at room temperature. Isopropyl amine (0.18 mL, 2.09 mmol) and acetic acid (0.15 mL) were added and the reaction was heated at 135° C. for an additional 18 h. The resultant solution was partitioned between ethyl acetate/water and 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 finally purified by flash column chromatography (10-100% ethyl acetate and hexane) then preparative HPLC (10-90% gradient of MeCN-water) to afford the title compound as a white solid: MS (ES) M+H expected 448.2, found 448.1.

後処理

  1. temperaturethe reaction was heated at 135° C. for an additional 18 h
  2. customThe resultant solution was partitioned between ethyl acetate/water
  3. washthe organic phase was washed with 1N HCl, saturated sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was finally purified by flash column chromatography (10-100% ethyl acetate and hexane)

出典と根拠

ORDレコード
ord-1c44fe10e66a424ba8d150a1a8ee1048
出典データセット
uspto-grants-2012_04
特許番号
US08153818B2

反応ノート

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