Potassium Carbonate → HCID 21996864, compound

HRID 1978186Notes

Reaction equation

HRID 1978186 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:32])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>CN(C)C=O>[F:22][C:23]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:24]=1[C:25]([N:10]1[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[NH:7][C:6]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:11]1)=[O:26]

Participants

5

Reactant 3

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

Product 1

HCID 21996864HCID 21996864, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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) as a white foam which crystallized by sonication from hexane-ethanol, m.p. 161-163° 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-4ccc1e532a394286b8d8c761475becaa
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

Loading…