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

HRID 1256185Notes

Reaction equation

HRID 1256185 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e64aa84016fb4ff7b0f1ebeca9d33bf2
Source dataset
uspto-grants-2013_06
Patent number
US08461178B2

Reaction notes

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