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

HRID 448110노트

반응식

HRID 448110 반응식
[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

참가 물질

7

반응물 4

HCID 6363IsopropylamineHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 593029884-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)benzenesulfonamide

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e836d72424b243df86e3b483facd887e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481579B2

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