Dichloromethane → N-[3-(2-{1,1-dimethyl-3-[4-(5-methyl-thiophen-2-yl)-imidazol-1-yl]-propylamino}-1-hydroxy-ethyl)-phenyl]-benzenesulphonamide

HRID 1010581노트

반응식

HRID 1010581 반응식
[OH:1][CH:2]([C:16]1[CH:17]=[C:18]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=1)[CH2:3][NH:4][C:5]([CH3:15])([CH3:14])[CH2:6][CH2:7][N:8]1[CH:12]=[C:11](I)[N:10]=[CH:9]1.C(=O)([O-])[O-].[Na+].[Na+].O1[CH2:43][CH2:42]OCC1.ClCCl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:14][C:5]([NH:4][CH2:3][CH:2]([C:16]1[CH:17]=[C:18]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:19]=[CH:20][CH:21]=1)[OH:1])([CH3:15])[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:26]2[S:23][C:42]([CH3:43])=[CH:28][CH:27]=2)[N:10]=[CH:9]1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 11497696N-(3-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-benzenesulphonamide

생성물 1

HCID 11713402N-[3-(2-{1,1-dimethyl-3-[4-(5-methyl-thiophen-2-yl)-imidazol-1-yl]-propylamino}-1-hydroxy-ethyl)-phenyl]-benzenesulphonamide수율 76%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매

실험 절차

0.277 g (0.500 mmol) N-(3-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-benzenesulphonamide, 0.807 g (0.613 mmol) 5-methylthiophene-2-boric acid, 0.031 g (0.038 mmol) [1,1′-bis(diphenylphosphino)ferrocene]-palladium(II)-chloride (1:1 complex with dichloromethane), 2.00 mL aqueous sodium carbonate solution (2M) and 2 mL dioxane were stirred for 5 min at 150° C. in a sealed reaction vessel in a microwave. The reaction mixture was cooled to ambient temperature and then poured into 20 mL dichloromethane and 20 mL water. The phases were separated, the organic phase was washed twice with 20 mL water, dried over magnesium sulphate and the solvent was eliminated using the rotary evaporator. The residue was purified by flash column chromatography [methylene chloride/methanol (100:0→75:25)]. 0.200 g (0.381 mmol, 76%) N-[3-(2-{1,1-dimethyl-3-[4-(5-methyl-thiophen-2-yl)-imidazol-1-yl]-propylamino}-1-hydroxy-ethyl)-phenyl]-benzenesulphonamide were obtained as a beige solid.

후처리

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 20 mL water
  3. dry with materialdried over magnesium sulphate
  4. customthe rotary evaporator
  5. customThe residue was purified by flash column chromatography [methylene chloride/methanol (100:0→75:25)]

출처 및 근거

ORD 기록
ord-a662039ca88c481cbb7990606d8bce37
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977334B2

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