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

HRID 1256185노트

반응식

HRID 1256185 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e64aa84016fb4ff7b0f1ebeca9d33bf2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461178B2

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