Dimethyl Sulfoxide → HCID 54514832, compound

HRID 2180082Notes

Reaction equation

HRID 2180082 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

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 EtOAc. The organic layer was washed with H2O (3×) then dried (Na2SO4), filtered and concentrated to an oil (90 mg, 0.253 mmol). (TLC 5% MeOH/CH2Cl2 (NH3) Rf 0.15).

Workup

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

Sources & evidence

ORD record
ord-8b4426412d994d32bb6ed5cbe08c262d
Source dataset
uspto-grants-2005_05
Patent number
US06887884B2

Reaction notes

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