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 1619641ノート

反応式

HRID 1619641 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9fb5823995d74fc28adf98e93ac92aba
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

反応ノート

読み込み中…