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2,2'-Bipyridine → Methyl 5-[methyl(ethylsulfonyl)amino]-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate

HRID 2252820
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HRID 2252820 반응식
Br[C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:27][NH:28][S:29]([CH2:32][CH3:33])(=[O:31])=[O:30].N1C=CC=CC=1C1C=CC=CN=1>[Cu-]=O.CN(C=O)C>[CH2:32]([S:29]([N:28]([CH3:27])[C:2]1[N:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[C:9]([O:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)(=[O:31])=[O:30])[CH3:33]
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6

반응물 3

HCID 14742,2'-BipyridineHCID 11105495N-methylethane-1-sulfonamideHCID 11339571Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

생성물 1

HCID 59645226Methyl 5-[methyl(ethylsulfonyl)amino]-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
118 °C

실험 절차

In a dried sealable pressure tube flushed with argon was placed methyl 5-bromo-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate (2.0 g, 4.57 mmol), prepared as described in Example 2, Step 2), N-methylethanesulfonamide (1.13 g, 9.15 mmol), dry DMF (4 mL) and copper(I) oxide (785 mg, 5.49 mmol) and 2,2′ bipyridyl (857 mg, 5.49 mmol). The tube was capped and heated to 118° C. for 2 hours. The reaction was cooled and filtered through a glass fiber filter, washing with chloroform. The filtrate was diluted with chloroform (about 100 mL total volume) and stirred with an EDTA solution (5 g EDTA in 100 mL water) for two hours or until the aqueous layer became aqua in color and the organic layer became yellow. The layers were separated and the aqueous layer was extracted twice more with chloroform. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was redissolved in 2 mL of DMSO and purified by preparative HPLC (Gilson semi preparative HPLC system using a Waters Nova pak column (10×40 mm I.D. cartridges, C18, 6 μM pore size) eluting with 95-5% water (0.025% TfEA)/acetonitrile (0.025% TFA) at 35 mLjmin) and the desired fractions were freeze dried to give the product as a yellow powder.

후처리

  1. customIn a dried sealable pressure tube flushed with argon
  2. customprepared
  3. customThe tube was capped
  4. temperatureThe reaction was cooled
  5. filtrationfiltered through a glass fiber
  6. filtrationfilter
  7. washwashing with chloroform
  8. additionThe filtrate was diluted with chloroform (about 100 mL total volume)
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted twice more with chloroform
  11. dry with materialThe combined organic extracts were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. dissolutionThe residue was redissolved in 2 mL of DMSO
  15. custompurified by preparative HPLC (Gilson semi preparative HPLC system
  16. washeluting with 95-5% water (0.025% TfEA)/acetonitrile (0.025% TFA) at 35 mLjmin) and the desired fractions
  17. customdried

출처 및 근거

ORD 기록
ord-366aea3a0dda41d0a581a77e6d2cb911
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07323460B2

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