Potassium Carbonate → HCID 10270942, compound

HRID 2375155Notes

Reaction equation

HRID 2375155 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+].[C:22]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:26][C:25]([C:28](Cl)=[O:29])=[CH:24][CH:23]=1>CN(C)C=O.O.ClCCl>[C:22]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:23]=[CH:24][C:25]([C:28]([N:10]2[CH2:11][C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:6]=3[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]2=3)=[O:29])=[CH:26][CH:27]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 841514-Phenylbenzoyl chlorideHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 10270942HCID 10270942, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5] benzodiazepine (1.0 g, 5.07 mmol) in N,N-dimethylformamide (10 mL) kept under nitrogen was added solid potassium carbonate (0.74 g, 5.35 mmol). The mixture was treated dropwise with a solution of 4-biphenylcarbonyl chloride (1.4 g, 6.46 mmol) in N,N-dimethylformamide (5 mL) and stirred at room temperature for 1 hour. The mixture was then diluted with water and extracted with ethyl acetate. The organic extracts were combined and washed with 1N sodium hydroxide, dried over anhydrous sodium sulfate and evaporated to dryness to give a pink foam which was purified by flash chromatography. Elution with 25% ethyl acetate in hexane provided a white foam which was redissolved in dichloromethane, concentrated in vacuo to a foam, then crystallized by sonication from ethyl acetate/hexane to give the title compound (1.28 g, 66.9%) as a white solid, m.p. 175-177° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 1N sodium hydroxide
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customto give a pink foam which
  6. customwas purified by flash chromatography
  7. washElution with 25% ethyl acetate in hexane
  8. customprovided a white foam which
  9. concentrationconcentrated in vacuo to a foam
  10. customcrystallized by sonication from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bf0de8d5baa4455097139825b4b34108
Source dataset
uspto-grants-2008_12
Patent number
US07465722B2

Reaction notes

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