1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11244088, compound

HRID 1351194Notes

Reaction equation

HRID 1351194 reaction equation
I[CH2:2][CH:3]1[CH2:14][C:13]2[C:15]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[CH:10]=[C:11]([O:18][CH3:19])[C:12]=2[O:16][CH3:17])[N:4]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:17][O:16][C:12]1[C:11]([O:18][CH3:19])=[CH:10][C:9]2=[C:15]3[C:13]=1[CH:14]=[C:3]([CH3:2])[N:4]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:5]3=[N:6][CH:7]=[N:8]2

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11385310HCID 11385310, compound

Product 1

HCID 11244088HCID 11244088, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To a solution 5-iodomethyl-7,8-dimethoxy-4-phenyl-5,6-dihydro-4H-1,3,4-triaza-phenalene (0.1 g, 0.22 mmol) (from Example 15, Step F, supra) in toluene (20 mL) was added DBU (73 μL, 0.49 mmol) (Fluka). The reaction mixture was heated at 120° C. for 1 hour. The mixture was then diluted with chloroform (100 mL), and washed with H2O. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:1:0.05) as eluent to give the desired 7,8-dimethoxy-5-methyl-4-phenyl-4H-1,3,4-triaza-phenalene as a pale yellow solid. (Yield 50 mg, 71%).

Workup

  1. washwashed with H2O
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-1f0021b20aef4373b9b9f1180503217c
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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