4-Toluenesulfonyl chloride → 2-(5-Benzyl-1,3,4-oxadiazol-2-yl)-6-bromo-5-(trifluoromethyl)pyridin-3-amine

HRID 574207ノート

反応式

HRID 574207 の反応式
[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)(Cl)Cl>[CH2:18]([C:17]1[O:14][C:13]([C:3]2[C:2]([NH2:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[C:5]([Br:12])[N:4]=2)=[N:15][N:16]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 867295943-Amino-6-bromo-N'-(2-phenylacetyl)-5-(trifluoromethyl)picolinohydrazide

生成物 1

HCID 715156962-(5-Benzyl-1,3,4-oxadiazol-2-yl)-6-bromo-5-(trifluoromethyl)pyridin-3-amine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
65 °C

実験手順

To a stirred suspension of 3-amino-6-bromo-N′-(2-phenylacetyl)-5-(trifluoromethyl) picolinohydrazide (106 mg, 0.254 mmol) in CHCl3 (2 ml) was added TEA (142 ul, 1.016 mmol) followed by TsCl (145 mg, 0.762 mmol). The mixture was heated to 65° C. for 3 h. The solvent was removed in vacuo and the resulting brown residue was suspended in EtOAc (10 ml). The mixture was washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 85% iso-hexane/EtOAc to afford the title compound as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 7.85 (1H, s), 7.39 (4H, m), 7.30 (3H, m), 4.45 (2H, s). LC-MS Rt=5.84 min [M+H]+ 401.0 Method 10minLC_v002.

後処理

  1. customThe solvent was removed in vacuo
  2. washThe mixture was washed with brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica eluting with 85% iso-hexane/EtOAc

出典と根拠

ORDレコード
ord-cd112c33554646009fa9673a92848a89
出典データセット
uspto-grants-2015_05
特許番号
US09034879B2

反応ノート

読み込み中…