N-bromobutanimide → HCID 67388478, compound

HRID 908483Notes

Reaction equation

HRID 908483 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:15]([C:16]2[O:17][C:18]3[C:24]([C:25]#[N:26])=[CH:23][CH:22]=[CH:21][C:19]=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:24]([C:25]#[N:26])=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:14][C:13]([Br:1])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 67388437HCID 67388437, compound

Product 1

HCID 67388478HCID 67388478, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-bromopyrrolidine-2,5-dione (44.5 mg) and 2-(2-amino-3-pyridyl)-1,3-benzoxazole-7-carbonitrile (59 mg) in tetrahydrofuran (5 ml) was stirred at room temperature for 1 hour. The reaction was incomplete and further 1-bromopyrrolidine-2,5-dione (44.5 mg) was added at room temperature and the reaction mixture was stirred at room temperature for 1 hour. The resulting precipitate was collected by filtration, washed with acetonitrile (2×2 ml) and dried to a constant weight to afford 2-(2-amino-5-bromo-3-pyridyl)-1,3-benzoxazole-7-carbonitrile (70.0 mg) as a pale brown solid. NMR Spectrum: (DMSOd6) 7.61 (dd, 1H), 7.85 (bs, 2H), 7.96 (dd, 1H), 8.20 (dd, 1H), 8.37 (d, 1H), 8.39 (d, 1H); Mass spectrum: M(+CH3CN)+H+ 356-358.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 hour
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with acetonitrile (2×2 ml)
  4. customdried to a constant weight

Sources & evidence

ORD record
ord-5ed09b9b8e0a4969bf83dc8f070b43a4
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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