Water → 1-(7-Bromo-[1,5]naphthyridin-2-yl)-3-phenethyl-urea

HRID 1256185ノート

反応式

HRID 1256185 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([NH2:12])=[N:9]2)=[N:4][CH:3]=1.ClC(Cl)(O[C:17](=[O:23])OC(Cl)(Cl)Cl)Cl.[C:25]1([CH2:31][CH2:32][NH2:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>N1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([NH:12][C:17]([NH:33][CH2:32][CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])=[N:9]2)=[N:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 1001PhenethylamineHCID 94429TriphosgeneHCID 583105327-Bromo-1,5-naphthyridin-2-amine

生成物 1

HCID 583105101-(7-Bromo-[1,5]naphthyridin-2-yl)-3-phenethyl-urea収率 24%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Under argon atmosphere, 201 mg (897 μmol, 1 eq) of 7-bromo-[1,5]naphthyridin-2-ylamine and 294 mg (993 μmol, 1.1 eq) of triphosgene were introduced in 10 mL of pyridine at 0° C. The mixture was stirred at reflux for 1 h. The mixture was allowed to reach rt and 238 μL (1.89 mmol, 2.1 eq) of 2-phenylethylamine were added. The mixture was stirred at reflux for 1 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with methylene chloride. Organic layers were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride/ethanol: 96/4 as eluent. The solvent was evaporated to dryness to afford 80 mg of yellow powder with 24% yield.

後処理

  1. temperatureat reflux for 1 h
  2. customto reach rt
  3. stirringThe mixture was stirred
  4. temperatureat reflux for 1 h
  5. customto reach rt
  6. extractionAqueous layer was extracted with methylene chloride
  7. dry with materialOrganic layers were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by column chromatography
  11. customThe solvent was evaporated to dryness

出典と根拠

ORDレコード
ord-e64aa84016fb4ff7b0f1ebeca9d33bf2
出典データセット
uspto-grants-2013_06
特許番号
US08461178B2

反応ノート

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