Potassium Carbonate → 5-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-[(3-pyridazin-4-ylbiphenyl-4-yl)oxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

HRID 1619641노트

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HRID 1619641 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:12]=2[OH:13])=[CH:3][N:2]=1.[Cl:20][C:21]1[C:22](F)=[CH:23][C:24]([F:47])=[C:25]([S:27]([N:30]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=2[O:45][CH3:46])[C:31]2[S:32][CH:33]=[N:34][N:35]=2)(=[O:29])=[O:28])[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:20][C:21]1[C:22]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8][C:7]=2[C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)=[CH:23][C:24]([F:47])=[C:25]([S:27]([N:30]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][C:38]=2[O:45][CH3:46])[C:31]2[S:32][CH:33]=[N:34][N:35]=2)(=[O:28])=[O:29])[CH:26]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 1362008863-Pyridazin-4-ylbiphenyl-4-ol

생성물 1

HCID 580422825-Chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-[(3-pyridazin-4-ylbiphenyl-4-yl)oxy]-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide수율 72.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

3-Pyridazin-4-ylbiphenyl-4-ol (Preparation 4, 50 mg, 0.2 mmol) and 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 16, 93 mg, 0.2 mmol) were dissolved in dimethylsulfoxide (2 mL). Potassium carbonate (83 mg, 0.6 mmol) was added and the reaction stirred at room temperature for 16 hours. The crude material was partitioned between ethyl acetate (20 mL) and water (20 mL), the organic layer separated, concentrated in vacuo and purified by silica gel column chromatography (ISCO™, 12 g silica, 0-100% ethyl acetate in heptane gradient elution). The appropriate fractions were combined and concentrated in vacuo to afford the title compound as a gum (100 mg, 72%).

후처리

  1. customThe crude material was partitioned between ethyl acetate (20 mL) and water (20 mL)
  2. customthe organic layer separated
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel column chromatography (ISCO™, 12 g silica, 0-100% ethyl acetate in heptane gradient elution)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9fb5823995d74fc28adf98e93ac92aba
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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