Potassium Carbonate → HCID 21996870, compound

HRID 1978204Notes

Reaction equation

HRID 1978204 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+].[Cl:22][C:23]1[CH:31]=[C:30]([C:32]2[N:36]=[C:35]([CH3:37])[N:34]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[N:33]=2)[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>CN(C)C=O.O>[Cl:22][C:23]1[CH:31]=[C:30]([C:32]2[N:36]=[C:35]([CH3:37])[N:34]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[N:33]=2)[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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 21996883HCID 21996883, compound

Product 1

HCID 21996870HCID 21996870, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine of Example 1, Step B (0.55 g, 2.8 mmol) in dimethylformamide (10 mL) under nitrogen was added solid potassium carbonate (0.39 g, 2.8 mmol). The mixture was treated dropwise with a solution of the crude acid chloride (2.8 mmol) of Step F in dimethylformamide (10 mL). After stirring at room temperature for 90 minutes, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined and washed with 1N aqueous sodium hydroxide, dried over sodium sulfate and evaporated to dryness. The residue was dissolved in dichloromethane and absorbed on a column of flash silica Merck-60. Less polar impurities were eluted with 1:1 ethyl acetate-hexane. Further elution with 2% methanol in dichloromethane provided the title compound as a white solid (0.57 g), m.p. 218-221° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 1N aqueous sodium hydroxide
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in dichloromethane
  6. customabsorbed on a column of flash silica Merck-60
  7. washLess polar impurities were eluted with 1:1 ethyl acetate-hexane
  8. washFurther elution with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-98f4863640b7448795ce74aa71c2c420
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

Loading…