Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate → Methyl 5-(1,1-dioxido-5-methyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy[1,6]-naphthyridine-7-carboxylate

HRID 897338노트

반응식

HRID 897338 반응식
Br[C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:17][N:18]1[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[NH:21][CH2:20][C:19]1=[O:27]>N1C=CC=CC=1.[Cu-]=O>[O:26]=[S:22]1(=[O:25])[CH2:23][CH2:24][N:18]([CH3:17])[C:19](=[O:27])[CH2:20][N:21]1[C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([OH:16])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

참가 물질

5

반응물 2

HCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylateHCID 223463175-Methyl-1,2,5-thiadiazepan-4-one 1,1-dioxide

생성물 1

HCID 22346441Methyl 5-(1,1-dioxido-5-methyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy[1,6]-naphthyridine-7-carboxylate

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 1049Pyridine용매

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온도
115 °C

실험 절차

A mixture of methyl 5-bromo-8-hydroxy[1,6]naphthyridine-7-carboxylate (0.28 g, 1.0 mmol), 5-methyl-1,2,5-thiadiazepan-4-one 1,1-dioxide from step 2 (0.178 g, 1.0 mmol) and copper (I) oxide (0.143 g, 1.0 mmol) in pyridine (5 mL) was heated in an oil bath at 115° C. overnight. The resultant mixture was filtered, and the filtrate concentrated under vacuum. The residue was treated with a mixture of chloroform (50 mL) and ethylenediamine tetraacetic acid, disodium salt (5 g) in water (30 mL) and stirred vigorously at room temp in the presence of air for 5 hours. The slurry was filtered through a pad of Celite. The organic extract was separated, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was triturated with methanol (25 mL) and the resultant suspension stirred at room temperature overnight. The solid was filtered, washed with cold (0° C.) methanol, and dried under vacuum to provide methyl 5-(1,1-dioxido-5-methyl-4-oxo-1,2,5-thiadiazepan-2-yl)-8-hydroxy[1,6]-naphthyridine-7-carboxylate as light brown solid.

후처리

  1. filtrationThe resultant mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. additionThe residue was treated with a mixture of chloroform (50 mL) and ethylenediamine tetraacetic acid, disodium salt (5 g) in water (30 mL)
  4. filtrationThe slurry was filtered through a pad of Celite
  5. extractionThe organic extract
  6. customwas separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue was triturated with methanol (25 mL)
  11. stirringthe resultant suspension stirred at room temperature overnight
  12. filtrationThe solid was filtered
  13. washwashed with cold (0° C.) methanol
  14. customdried under vacuum

출처 및 근거

ORD 기록
ord-1b719b32ae9f471196c0c9620cc69403
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921759B2

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