Sodium Hydroxide → 3-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 659686

반응식

HRID 659686 반응식
[Br:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[OH-].[Na+].Br[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:21]=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:19][C:18]=2[S:26]([NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:28])=[O:27])[CH:14]=[CH:15][CH:16]=1>CS(C)=O.C(Cl)Cl>[Br:1][C:2]1[N:3]([CH2:10][C:11]2[CH:12]=[C:13]([C:17]3[CH:21]=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[S:19][C:18]=3[S:26]([NH:29][C:30]([CH3:32])([CH3:31])[CH3:33])(=[O:27])=[O:28])[CH:14]=[CH:15][CH:16]=2)[CH:4]=[CH:5][N:6]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 27732612-Bromo-1H-imidazoleHCID 670039813-(3-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

생성물 1

HCID 671329713-[3-(2-bromoimidazol-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide수율 99%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-bromoimidazole (68.9 mg, 0.469 mmol; see step (a)) in DMSO (1 mL) and NaOH (32.8 mg, 0.82 mmol), that had been stirred for 40 min at ambient temperature, was added a solution of 3-(3-bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (173.6 mg, 0.391 mmol; see Example 1(e)) in DMSO (1 mL) dropwise. The reaction mixture was stirred for 1 h at ambient temperature and then diluted with CH2Cl2 (15 mL). The organic layer was washed with water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (3:97) as eluent to give the sub-title compound in 99% yield as a colourless syrup (197.3 mg, 0.387 mmol).

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

출처 및 근거

ORD 기록
ord-65988bf132aa4dc887dfc212dc2bf758
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080571B2

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