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 2196605노트

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HRID 2196605 반응식
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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-627973c679e6412c8e7865dfa184c317
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338460B2

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