N-bromobutanimide → HCID 86714187, compound

HRID 920086Notes

Reaction equation

HRID 920086 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:28])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[C:10](=[O:21])[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:8]2)=[O:4].[Br:29]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:28])=[C:7]2[C:12](=[C:13]([Br:29])[N:14]=1)[N:11]([CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1)[C:10](=[O:21])[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:8]2)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68297399HCID 68297399, compound

Product 1

HCID 86714187HCID 86714187, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-cyclopentylmethyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (147 mg, 0.39 mmol) and N-bromosuccinimide (76 mg, 0.43 mmol) in CH2Cl2 (1.5 mL) was refluxed for 3 h. Solvent was evaporated in vacuo, and the residue was purified by silica gel chromatography (5-15% EtOAc/hexanes+1% AcOH) to give 127 mg of the title compound as a yellow solid. MS: (−) m/z 455.21, 457.17 (M-1, 79/81Br).

Workup

  1. temperaturewas refluxed for 3 h
  2. customSolvent was evaporated in vacuo
  3. customthe residue was purified by silica gel chromatography (5-15% EtOAc/hexanes+1% AcOH)

Sources & evidence

ORD record
ord-02d92a4985464ee9ae38556596b4e907
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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