Dimethylformamide → HCID 21254872, compound

HRID 2288682Notes

Reaction equation

HRID 2288682 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[C:23]1[CH:24]=[CH:25][C:26]([CH3:32])=[C:27]([CH:31]=1)[C:28](Cl)=[O:29].C[N:34]([CH3:37])C=O>O.ClCCl>[N:1]1[C:6]2[NH:7][C:8]3[C:15]([C:28]([C:27]4[CH:31]=[C:23]([N:34]5[CH:37]=[CH:9][C:8]([CH3:15])=[N:7]5)[CH:24]=[CH:25][C:26]=4[CH3:32])=[O:29])=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 27373835-Fluoro-2-methylbenzoyl chlorideHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 21254872HCID 21254872, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 (55.8%) 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-f6de6138f7da40728d29a944d7f97d78
Source dataset
uspto-grants-2000_07
Patent number
US06090803

Reaction notes

Loading…