N-bromobutanimide → 3-(5-Bromo-4-methoxy-imidazo[5,1-f][1,2,4]triazin-7-yl)-cyclobutanone

HRID 449015Notes

Reaction equation

HRID 449015 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[C:16]2=[CH:17][N:18]=[C:19]([CH:20]3[CH2:23][C:22](=[O:24])[CH2:21]3)[N:15]2[N:14]=[CH:13][N:12]=1>CN(C=O)C>[Br:8][C:17]1[N:18]=[C:19]([CH:20]2[CH2:23][C:22](=[O:24])[CH2:21]2)[N:15]2[C:16]=1[C:11]([O:10][CH3:9])=[N:12][CH:13]=[N:14]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 669155953-(4-Methoxyimidazo[5,1-f][1,2,4]triazin-7-yl)cyclobutanone

Product 1

HCID 669155063-(5-Bromo-4-methoxy-imidazo[5,1-f][1,2,4]triazin-7-yl)-cyclobutanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (2.00 g, 0.01 mol) was added in one portion to a stirred, cooled solution of 3-(4-methoxyimidazo[5,1-f][1,2,4]triazin-7-yl)cyclobutanone (6.0 g, 0.027 mol) in DMF (40 mL) at 0° C. under N2. Two other portions of NBS (2.00 g, 0.01 mol) were added after 15 and 30 min respectively. The reaction was stirred with cooling for 5 h. The reaction mixture was partitioned between EtOAc (1 L) and brine (200 mL) and then 83 of 219 organic layer was washed with brine (2×150 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using hexanes:EtOAc (1:1) as the eluent. 1H NMR (400 MHz, Chloroform-d) δ 3.45-3.60 (m, 3H), 3.66-3.77 (m, 2H), 4.19 (s, 3H), 8.01 (s, 1H).

Workup

  1. temperaturewith cooling for 5 h
  2. customThe reaction mixture was partitioned between EtOAc (1 L) and brine (200 mL)
  3. wash83 of 219 organic layer was washed with brine (2×150 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f6b7d1f06fff48f483d6302836c46b40
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…