Cesium carbonate → 3-{[4-(2-methoxyethoxy)phenyl]thio}-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

HRID 2196605ノート

反応式

HRID 2196605 の反応式
Br[CH2:2][CH2:3][O:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[C:21]([C:33]([NH:35][C:36]3[S:40][N:39]=[C:38]([CH3:41])[N:37]=3)=[O:34])=[N:22][C:23]([S:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][N:28]=3)=[CH:24][CH:25]=2)=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:5][O:4][CH2:3][CH2:2][O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19][C:20]2[C:21]([C:33]([NH:35][C:36]3[S:40][N:39]=[C:38]([CH3:41])[N:37]=3)=[O:34])=[N:22][C:23]([S:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][N:28]=3)=[CH:24][CH:25]=2)=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 809722-Bromoethyl methyl etherHCID 597062523-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

生成物 1

HCID 597062533-{[4-(2-methoxyethoxy)phenyl]thio}-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

0.43 ml of 1-bromo-2-methoxyethane and 4.99 g of cesium carbonate were added to a dimethylformamide (20 ml) solution of 2 g of 3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide obtained in Reference Example (step 3), and stirred at 60° C. for 1 hour. At room temperature, aqueous saturated ammonium chloride solution was added to it, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol) and crystallized from ethanol to obtain 1.43 g of the entitled compound as a yellow solid.

後処理

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline water
  3. dry with materialThis was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol)
  6. customcrystallized from ethanol

出典と根拠

ORDレコード
ord-627973c679e6412c8e7865dfa184c317
出典データセット
uspto-grants-2012_12
特許番号
US08338460B2

反応ノート

読み込み中…