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

HRID 2252820
ノート
印刷プレビュー

反応式

HRID 2252820 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178419072HCID 178419072、化合物触媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
118 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-366aea3a0dda41d0a581a77e6d2cb911
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07323460B2

反応ノート

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