N-bromobutanimide → HCID 10237594, compound

HRID 1814890Notes

Reaction equation

HRID 1814890 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][NH:15][C:16]([C:18]2[C:19](=[O:28])[C:20]3[CH:27]=[CH:26][O:25][C:21]=3[N:22]([CH3:24])[CH:23]=2)=[O:17])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[Br:1][C:26]1[O:25][C:21]2[N:22]([CH3:24])[CH:23]=[C:18]([C:16]([NH:15][CH2:14][C:13]3[CH:12]=[CH:11][C:10]([Cl:9])=[CH:30][CH:29]=3)=[O:17])[C:19](=[O:28])[C:20]=2[CH:27]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22498719HCID 22498719, compound

Product 1

HCID 10237594HCID 10237594, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

N-Bromosuccinimide (2.77 g) was added to a solution of N-(4-chlorobenzyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 78, 2.46 g) in CHCl3 (100 mL). The reaction mixture was heated to 50° C. for 18 h. The mixture was allowed to cool to room temperature and was washed with water (100 mL) and brine (100 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol, 99/1) followed by recrystallization from ethyl acetate to yield 1.87 g (61%) of the title compound as a white solid. Physical characteristics. M.p. 232-233° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.50, 8.57, 7.41-7.32, 7.23, 4.55, 3.92; MS (EI) m/z 394 (M+), 396 (M++2).

Workup

  1. temperatureto cool to room temperature
  2. washwas washed with water (100 mL) and brine (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol, 99/1)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-0a075bef61b245ffb99d40ab49c161fd
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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