N-bromobutanimide → HCID 67388363, compound

HRID 908432Notes

Reaction equation

HRID 908432 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:15]([C:16]2[O:17][C:18]3[C:19](=[C:21]([C:25]#[N:26])[CH:22]=[CH:23][CH:24]=3)[N:20]=2)=[CH:14][CH:13]=[CH:12][N:11]=1>O1CCCC1>[NH2:9][C:10]1[C:15]([C:16]2[O:17][C:18]3[C:19](=[C:21]([C:25]#[N:26])[CH:22]=[CH:23][CH:24]=3)[N:20]=2)=[CH:14][C:13]([Br:1])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67388481HCID 67388481, compound

Product 1

HCID 67388363HCID 67388363, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

1-Bromopyrrolidine-2,5-dione (199 mg) was added to a stirred solution of 2-(2-amino-3-pyridyl)-1,3-benzoxazole-4-carbonitrile (240 mg) dissolved in tetrahydrofuran (5 ml) over a period of 5 minutes. The resulting solution was stirred at 25° C. for 2 hours. The solvent was evaporated and the residue was washed with water. The residue was basified with 7 M ammonia in methanol and adsorbed on silica gel with methylene chloride. The crude product was purified by flash chromatography on silica gel eluting with 1 to 2% methanol in dichloromethane. The solvent was evaporated to dryness to afford 2-(2-amino-5-bromopyridin-3-yl)benzo[d]oxazole-4-carbonitrile (205 mg) as a solid. NMR Spectrum: (CDCl3): 7.47 (dd, 1H), 7.70 (dd, 1H), 7.82 (dd, 1H), 7.97 (bs, 2H), 8.31 (d, 1H), 8.41 (d, 1H); Mass spectrum: M+H+ 315-317

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. customThe crude product was purified by flash chromatography on silica gel eluting with 1 to 2% methanol in dichloromethane
  4. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-bd52f6a5ea9d4f5ba0ed12172c206c4e
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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