Hydrochloric Acid → HCID 66834590, compound

HRID 61789Notes

Reaction equation

HRID 61789 reaction equation
C[O:2][C:3](=[O:30])[C:4]#[C:5][C:6]1[C:27]([O:28][CH3:29])=[CH:26][C:9]2[C:10]([CH3:25])([CH3:24])[C:11]3[NH:12][C:13]4[C:18]([C:19]=3[C:20](=[O:21])[C:8]=2[CH:7]=1)=[CH:17][CH:16]=[C:15]([C:22]#[N:23])[CH:14]=4.Cl>CO.C1COCC1.[OH-].[K+]>[C:22]([C:15]1[CH:14]=[C:13]2[C:18]([C:19]3[C:20](=[O:21])[C:8]4[CH:7]=[C:6]([C:5]#[C:4][C:3]([OH:30])=[O:2])[C:27]([O:28][CH3:29])=[CH:26][C:9]=4[C:10]([CH3:24])([CH3:25])[C:11]=3[NH:12]2)=[CH:17][CH:16]=1)#[N:23]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66834050HCID 66834050, compound

Product 1

HCID 66834590HCID 66834590, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 14797Potassium HydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3-Cyano-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl)-propynoic acid methyl ester (Compound E6-1, 15.2 mg, 0.038 mmol) was dissolved in a mixture solvent of methanol (1.5 mL) and THF (0.5 mL), added with 2 N aqueous solution of potassium hydroxide (5 drops), and then stirred at room temperature overnight. 0.5 N Hydrochloric acid was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solids obtained after filtration and concentration under reduced pressure were washed with dichloromethane and purified by HPLC to obtain the title compound (white solid, 9.6 mg, 66%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solids obtained
  5. filtrationafter filtration and concentration under reduced pressure
  6. washwere washed with dichloromethane
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-6ea983a8eeac40a4bd002d1102536314
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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