Dimethylformamide → HCID 9887157, compound

HRID 636373Notes

Reaction equation

HRID 636373 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+].[F:22][C:23]1[CH:31]=[C:30](F)[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].C[N:34]([CH3:37])C=O>>[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[N:10]([C:25]([C:24]3[CH:28]=[CH:29][C:30]([N:34]4[CH:37]=[CH:9][C:8]([CH3:15])=[N:7]4)=[CH:31][C:23]=3[F:22])=[O:26])[CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 5880812,4-Difluorobenzoyl chlorideHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 9887157HCID 9887157, compoundYield 51%

Procedure

To a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine of Example 1, Step B (3.0 g, 15.2 mmol) in dimethylformamide (35 mL) under nitrogen was added potassium carbonate (6.3 g, 45.6 mmol) followed by a solution of the crude 2,4-difluorobenzoylchloride of Step A (22.8 mmol) in dimethylformamide (15 mL). After stirring at room temperature for 20 minutes, the reaction mixture was washed with water and stirred to give a solid which was collected by filtration. The solid was dissolved in chloroform and washed with 1 N sodium hydroxide and brine. The organic phase was dried over sodium sulfate and evaporated to dryness. The crude material was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 20% ethyl acetate in hexane provided the title compound (2.6 g, 51%) as a white foam which crystallized by sonication from hexane-ethanol, m.p. 16114 163° C.

Workup

  1. washthe reaction mixture was washed with water
  2. stirringstirred
  3. customto give a solid which
  4. filtrationwas collected by filtration
  5. dissolutionThe solid was dissolved in chloroform
  6. washwashed with 1 N sodium hydroxide and brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. customevaporated to dryness
  9. dissolutionThe crude material was dissolved in dichloromethane
  10. customabsorbed onto a silica Merck-60 flash column
  11. washElution with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ca557f7352db42e88b93e777f8cf47e3
Source dataset
uspto-grants-2001_02
Patent number
US06194407B1

Reaction notes

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