Triethylamine → 3-(2-Fluoro-4-iodophenyl)-4-fluoro-8-methyl-1H-imidazo[4,5-g]quinazolin-2(3H)-one

HRID 558249Notes

Reaction equation

HRID 558249 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]([F:20])=[C:18]2[C:13]([C:14]([CH3:21])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1C(O)=O.C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2[C:11](=[CH:12][C:13]3[C:14]([CH3:21])=[N:15][CH:16]=[N:17][C:18]=3[C:19]=2[F:20])[NH:27][C:30]1=[O:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 595194867-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acid

Product 1

HCID 595194923-(2-Fluoro-4-iodophenyl)-4-fluoro-8-methyl-1H-imidazo[4,5-g]quinazolin-2(3H)-oneYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 7-(2-fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazoline-6-carboxylic acid (190 mg, 0.47 mmol) in toluene (10 ml) was added triethylamine (0.19 ml, 1.41 mmol) and diphenylphosphoryl azide (0.20 ml, 0.94 mmol). The reaction was heated at reflux for 4 h. The mixture was cooled to room temperature and concentrated to dryness. Silica gel chromatography (EtOAc:Hexane=75:25) yields 143 mg (75%) of the title compound as a tan solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 h
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2338a7a50b234ca7bb76913c34192fa5
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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