Sodium Iodide → HCID 66748456、化合物

HRID 1405716

反応式

HRID 1405716 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[I-].[Na+].[O:16]=[S:17]1(=[O:34])[CH2:22][CH2:21][N:20]2[CH:23]=[CH:24][CH:25]=[C:26]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[C:19]2=[N:18]1.[OH-].[Na+]>CS(C)=O>[O:11]1[CH2:12][CH2:13][CH:8]([O:33][C:30]2[CH:29]=[CH:28][C:27]([C:26]3[C:19]4=[N:18][S:17](=[O:34])(=[O:16])[CH2:22][CH2:21][N:20]4[CH:23]=[CH:24][CH:25]=3)=[CH:32][CH:31]=2)[CH2:9][CH2:10]1

参加物

7

反応物 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 133496544-BromotetrahydropyranHCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

生成物 1

HCID 66748456HCID 66748456、化合物収率 17%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
160 °C

実験手順

A mixture of potassium carbonate (750 mg), 4-bromotetrahydro-2H-pyran (896 mg), sodium iodide (814 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) in DMSO (5 mL) was stirred at 150° C. overnight and 160° C. for 24 hr. The mixture was poured into 1N NaOH aq. and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) to give a white solid (66.6 mg). The solid was purified by preparative HPLC (C18, eluted with H2O in acetonitrile containing 0.1% TFA). The desired fraction was neutralized with sat. NaHCO3 aq. and extracted with EtOAc. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (17.0 mg) as a white solid.

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH aq. and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)

出典と根拠

ORDレコード
ord-2e38f30372214319bee7d739ba491561
出典データセット
uspto-grants-2014_12
特許番号
US08916551B2

関連ノート

読み込み中…