Dimethyl Sulfoxide → HCID 54514832, compound

HRID 10089Notes

Reaction equation

HRID 10089 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:21][CH:20]2[CH2:22][CH:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][C:19]=32)[N:16]=[C:15]([CH3:23])[NH:14]4)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.I[CH2:29][CH2:30][CH3:31].O>[OH-].[Na+].CO.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH2:22][CH:20]([C:19]3[CH:18]=[C:17]4[C:13](=[CH:12][C:11]=32)[N:14]=[C:15]([CH3:23])[N:16]4[CH2:29][CH2:30][CH3:31])[CH2:21]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 336431-IodopropaneHCID 543110386-Methyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester

Product 1

HCID 54514832HCID 54514832, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
40 °C

Procedure

(For conditions, see; Pilarski, B. Liebigs Ann. Chem. 1983, 1078.) 6-Methyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester (80 mg, 0.267 mmol) was stirred in 50% aqueous NaOH solution (3 mL) and DMSO (1 mL) then treated with 1-iodopropane (0.03 mL, 0.321 mmol). This mixture was warmed to 40° C. for 2 hours then cooled, treated with H2O and extracted with ethyl acetate. The organic layer was washed with H2O (3 times) then dried (Na2SO4), filtered and concentrated to an oil (90 mg, 0.253 mmol). (TLC 5% methanol/CH2Cl2 (NH3) Rf 0.15).

Workup

  1. temperaturethen cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with H2O (3 times)
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c87a28432656476ca44431e7feb16a78
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Reaction notes

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