Potassium Carbonate → HCID 178497978, compound

HRID 2298813Notes

Reaction equation

HRID 2298813 reaction equation
Br[CH:2]1[C:8](=O)[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([C:14]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([O:26][CH3:27])[CH:17]=2)=[O:15])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl.[C:35]([NH2:38])(=[NH:37])[CH3:36]>C(#N)C.C(Cl)(Cl)Cl>[CH3:36][C:35]1[NH:37][C:8]2[C:7]3[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=3[N:5]([C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([O:26][CH3:27])[CH:17]=3)=[O:15])[CH2:4][CH2:3][C:2]=2[N:38]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67170Acetamidine monohydrochlorideHCID 18378632HCID 18378632, compound

Product 1

HCID 178497978HCID 178497978, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of methyl 4-(4-bromo-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl-2-methoxybenzoate (240 mg) and potassium carbonate (767 mg) in acetonitrile (8 ml) was added acetamidine hydrochloride (472 mg) and the mixture was heated at 90° C. for 3 hours. After cooling, the reaction mixture was diluted with chloroform and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography (SiO2; 30 g, ethyl acetate) to give methyl 4-(2-methyl-1,4,5,6-tetrahydro-imidazo[4,5-d][1]benzazepin-6-yl)carbonyl-2-methoxybenzoate (95 mg).

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by column chromatography (SiO2; 30 g, ethyl acetate)

Sources & evidence

ORD record
ord-6a2f09798e7c45e2aecf658c56b9dcc0
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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