Sodium Hydroxide → HCID 13629282, compound

HRID 746806Notes

Reaction equation

HRID 746806 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([C:24]([OH:26])=[O:25])=[CH:16][CH:17]=[C:18](SC)[C:19]=2C#N)=[CH:10][CH:9]=1.C1CCN2C(=NCCC2)CC1.ClS(C(C)C)(=O)=O.[OH-].[Na+]>CO.ClCCl.CO.C(Cl)Cl>[C:14]1([C:11]2[CH:12]=[CH:13][C:8]([C:3]3[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:9][CH:10]=2)[C:15]([C:24]([OH:26])=[O:25])=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 824082-Propanesulfonyl chloride2×HCID 69254526HCID 69254526, compound

Product 1

HCID 13629282HCID 13629282, compoundYield 5.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

Mix 2″-Amino-6-cyano-5-methylsulfanyl-[1,1′;4′,1″]terphenyl-2-carboxylic acid (0.195 g, 0.521 mmol) and dichloromethane (6 ml) then cool to 0° C. Next add DBU (0.33 ml, 2.162 mmol), and ClSO2CH(CH3)2 (0.13 ml, 1.128 mmol) drop wise to the solution and stir for 16 hours. If TLC shows remaining SM, add DBU (0.3 ml) and ClSO2CH(CH3)2 (0.1 ml) and stir for 16 hours. Dilute the reaction with CH2Cl2 (50 ml) and wash with H2O, satd aq. sodium chloride, dry with Na2SO4, and concentrate under reduced pressure. Analyze by TLC and if reaction has remaining SM add MeOH (2 ml) and 1N NaOH (1 ml, 1 mmol). Heat to reflux for 6 hours. Add 1N HCL (1 ml, 1 mmol) and extract into dichloromethane. Purify the reaction by flash chromatography (Silica gel -dichloromethane then up to 10% MeOH/dichloromethane), to give 6-Cyano-5-methylsulfanyl-3″-propane-2-sulfonylamino)-[1,1′;4′,1″]terphenyl-2-carboxylic acid (0.008 g). MS (m/e): 467(M+1).

Workup

  1. additionDilute
  2. washwash with H2O
  3. dry with materialdry with Na2SO4
  4. concentrationconcentrate under reduced pressure
  5. customAnalyze by TLC and if reaction
  6. temperatureHeat
  7. temperatureto reflux for 6 hours
  8. additionAdd 1N HCL (1 ml, 1 mmol)
  9. extractionextract into dichloromethane
  10. customPurify
  11. customthe reaction by flash chromatography (Silica gel -dichloromethane

Sources & evidence

ORD record
ord-2ef79f5f57fa4ec58a25e02b9ffb9dc7
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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