Imidazole → HCID 19427681, compound

HRID 1078546Notes

Reaction equation

HRID 1078546 reaction equation
[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](OS(C(F)(F)F)(=O)=O)=[N:7][C:6]3[C:23]([CH3:27])=[CH:24][CH:25]=[N:26][C:5]2=3)[CH2:3][CH2:2]1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1>O1CCOCC1>[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8]([N:28]3[CH:32]=[CH:31][N:30]=[CH:29]3)=[N:7][C:6]3[C:23]([CH3:27])=[CH:24][CH:25]=[N:26][C:5]2=3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 19427680HCID 19427680, compound

Product 1

HCID 19427681HCID 19427681, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 11-cyclopropyl-4-methyl-6-trifluoromethanesulfonyloxy-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine (0.12 g, 0.3 mmol) in dioxan (1 mL) was added imidazole (0.06 g, 0.88 mmol). The mixture was heated at 100° C. for 10 min. After cooling to room temperature, the reaction mixture was diluted with ethyl adetate, washed with water, dried over sodium sulfate, filtered and concentrated. The residue was fractionated by preparative layer chromatography (silica gel, eluted with 67% ethyl acetate/hexane) to give the title compound (0.04 g, 0.12 mmol, 42%) which crystallized from di-isopropyl ether, m.p. 198°-200° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was diluted with ethyl adetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe residue was fractionated by preparative layer chromatography (silica gel, eluted with 67% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3b16c01633f34d35aa0a5c6692c1f568
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

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