hydroxylamine-O-sulfonic acid → 4-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamide

HRID 1353001ノート

反応式

HRID 1353001 の反応式
C[S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=[C:12]2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:26][Si:27]([CH3:55])([CH3:54])[CH2:28][CH2:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[N:41]=[C:40]2[C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[CH:35][CH:34]=1)(=[O:32])=[O:31].[N+:56](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(=O)C.[Na+].NOS(O)(=O)=O>C1COCC1.O.C(OCC)(=O)C>[CH3:26][Si:27]([CH3:55])([CH3:54])[CH2:28][CH2:29][S:30]([C:33]1[CH:34]=[CH:35][C:36]([N:39]2[CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[N:41]=[C:40]2[C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[CH:37][CH:38]=1)(=[O:31])=[O:32].[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:12]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([NH2:56])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[N:13]=2)[CH:21]=1

参加物

10

反応物 5

HCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 9929140HCID 9929140、化合物HCID 105276743-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

生成物 2

HCID 97993874-(2-Pyridin-3-yl-4-trifluoromethyl-imidazol-1-yl)-benzenesulfonamide収率 87%HCID 105276743-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-[1-[4-[[2-(Trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine was prepared with the product of Example 28 with a method similar to that described in Example 45, Step 1. To a solution of 3-[1-[4-[[2-(trimethylsilyl)ethyl]sulfonyl]phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (0.200 g, 0.46 mmol) in 1.0 mL of dry THF was added n-Bu4NF (1.38 mL of 1.0 M THF solution, 1.38 mmol). The mixture was heated to reflux for 1 hour and cooled to room temperature. A solution of sodium acetate (0.17 g, 2.1 mmol) in 3 mL of water and hydroxylamine-O-sulfonic acid (0.26 g, 2.3 mmol) were added sequentially and the mixture was stirred for 1 hour. Water (7 mL) and ethyl acetate (7 mL) were added. The organic phase was separated and washed with saturated NaHCO3 solution, water, brine, dried over MgSO4 and filtered. The filtrate was concentrated and the residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5) to give 0.147 g of 4-[2-(pyridin-3-yl)-4-(trifluoromethyl)-1H-imidazol-1-yl]benzenesulfonamide as a colorless solid (87%): mp(DSC) 213–215° C. Anal. Calc'd. for C15H11F3N4O2S: C, 48.91; H. 3.01; N, 15.21; S, 8.71. Found: C, 48.58; H, 2.99; N, 14.87; S. 8.85.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 solution, water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue was purified by chromatography on silica gel (ethyl acetate/acetone, 95:5)

出典と根拠

ORDレコード
ord-b6e10e9b9be147319f200186f2f7ea69
出典データセット
uspto-grants-2007_05
特許番号
US07220770B2

反応ノート

読み込み中…