Hydrogen Bromide → HCID 57586731, compound

HRID 1097739Notes

Reaction equation

HRID 1097739 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][N:16]=2)[C:11]([S:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)=[CH:10][C:9]1=[O:26])C1C=CC=CC=1.Br.[OH-].[Na+]>O>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([S:18][C:11]2[C:12]3[C:17](=[N:16][CH:15]=[CH:14][CH:13]=3)[NH:8][C:9](=[O:26])[CH:10]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 57586716HCID 57586716, compound

Product 1

HCID 57586731HCID 57586731, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-benzyl-4-(4-bromo-phenylsulfanyl)-1H-[1,8]naphthyridin-2-one (200 mg, 0.47 mmol) and HBr (5 mL, 48%) was heated under reflux for 4 h. After cooling, water was added and the mixture was neutralized with NaOH. The mixture was extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. After removal of solvent, the solid was recrystallized with EtOAc and hexane to give 30 mg of product (Yield: 19%). Note: the solubility of the product in organic solvent is poor. 1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.58 (d, J=4.0 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 7.76 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.0 Hz, 2H), 7.29 (dd, J=8.0, 5.0 Hz, 1H), 5.74 (s, 1H); LCMS (EI) m/z 332.8 (M+), 334.9.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter removal of solvent
  8. customthe solid was recrystallized with EtOAc and hexane

Sources & evidence

ORD record
ord-55beafa77ef2462abad85e25dccb40bc
Source dataset
uspto-grants-2012_03
Patent number
US08143276B2

Reaction notes

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