Potassium Carbonate → HCID 21996882, compound

HRID 1978189Notes

Reaction equation

HRID 1978189 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:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28](Cl)=[O:29]>CN(C)C=O.O.ClCCl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([C:28]([N:10]2[C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:11]2)=[O:29])[CH:31]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27373835-Fluoro-2-methylbenzoyl chlorideHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 21996882HCID 21996882, compoundYield 55.8%

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 of Example 1, Step B (2.0 g, 10.1 mmol) in dimethylformamide (15 mL) under nitrogen was added potassium carbonate (4.1 g, 29.7 mmol). The mixture was treated dropwise with a solution of crude 5-fluoro-2-methyl benzoyl chloride of Step A (15.0 mmol) in dimethylformamide (10 mL). After stirring at room temperature for 15 minutes, the mixture was diluted with water and stirred to give a solid mass which was collected by filtration. The solid was dissolved in chloroform and washed with 1 N sodium hydroxide and brine. The organic layer was dried over sodium sulfate and evaporated to dryness to give a purple oil. The crude material was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 20% ethyl acetate in hexane provided 1.88 g of the title product as a foam which was crystallized by sonication from ethanol-hexane, m.p. 138-140° C.

Workup

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

Sources & evidence

ORD record
ord-d1b2477491014774b00c3db72f8a9ea9
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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