4-(Trifluoromethyl)benzenesulfonamide → N-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-(trifluoromethyl)benzenesulfonamide

HRID 1062429

반응식

HRID 1062429 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([C:13]([OH:15])=O)[N:12]=1.N=C=N.[F:26][C:27]([F:39])([F:38])[C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH2:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([C:13]([NH:37][S:34]([C:31]2[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:39])[F:38])=[CH:33][CH:32]=2)(=[O:35])=[O:36])=[O:15])[N:12]=1

참가 물질

6

반응물 3

HCID 700184-(Trifluoromethyl)benzenesulfonamideHCID 160435CarbodiimideHCID 218688042-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid

생성물 1

HCID 22285489N-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-(trifluoromethyl)benzenesulfonamide수율 10%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

In a 20-mL screw-cap vial, 250 mg (0.75 mmol) 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid, 18.3 mg DMAP (0.15 mmol), 1.25 g PS-Carbodimide (1.5 mmol) (polystyrene-supported cyclohexylcarbodiimide, Argonaut Technologies Inc., San Carlos, Calif.), 169 mg α,α,α-trifluoro-p-toluenesulfonamide (0.75 mmol), and 12 mL dichloromethane were added, and the reaction mixture was mixed by orbital shaking at rt overnight. The reaction mixture was filtered through a filter tube (polypropylene frit), and the filtrate was evaporated under reduced pressure. The crude product was redissolved in 2 mL MeOH and purified by preparative HPLC to give 39.3 mg of N-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-(trifluoromethyl)benzenesulfonamide (beige solid, 10% yield). 1H NMR (400 MHz, CD3COCD3) δ 8.25 (d, 2 H), 7.85 (s, 1 H), 7.75 (s, 2H), 7.20-7.40 (m, 6 H), 6.95 (t, 2 H); LC-MS m/z 540 (MH+), retention time 3.36 min (method 2).

후처리

  1. customIn a 20-mL screw-cap vial
  2. additionthe reaction mixture was mixed
  3. filtrationThe reaction mixture was filtered through a filter tube (polypropylene frit)
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe crude product was redissolved in 2 mL MeOH
  6. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-bc29e7eca9224b2b8473d81bd2bf616f
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960601B2

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