Water → HCID 21696873, compound

HRID 378897

Reaction equation

HRID 378897 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Br:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[C:25]([Cl:32])[CH:24]=1.O>CN(C)C=O>[Br:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([C:15]2[C:8]3[NH:7][C:6]4[N:1]=[CH:2][CH:3]=[CH:4][C:5]=4[CH2:11][NH:10][C:9]=3[CH:12]=[CH:13][CH:14]=2)=[O:28])=[C:25]([Cl:32])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 15592207HCID 15592207, compound

Product 1

HCID 21696873HCID 21696873, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5] benzodiazepine (3 g, 15.2 mmol) in N,N-dimethylformamide under nitrogen were added solid potassium carbonate (6.3 g, 45.6 mmol). The mixture was treated dropwise with a solution of the crude 4-bromo-2-chlorobenzoyl chloride (22.9 mmol) in N,N-dimethylformamide. After stirring at room temperature for 15 minutes, water was added under stirring. The resulting solid was collected, dissolved in chloroform, and the solution washed with 1N NaOH and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue (purple foam) was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 20% ethyl acetate in hexane provided 3.4 g of the title compound as a foam which crystallized as a white solid by trituration from ethanol-ether, m.p. 165-168° C.

Workup

  1. stirringunder stirring
  2. customThe resulting solid was collected
  3. dissolutiondissolved in chloroform
  4. washthe solution washed with 1N NaOH and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. dissolutionThe residue (purple foam) was dissolved in dichloromethane
  8. customabsorbed onto a silica Merck-60 flash column
  9. washElution with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-cbe60203604a4ead849d41dddccd377c
Source dataset
uspto-grants-2001_10
Patent number
US06297234B1

Linked notes

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