1,1'-Carbonyldiimidazole → HCID 66692141, compound

HRID 710555Notes

Reaction equation

HRID 710555 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[C:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)=[N:21][CH:22]=2)=[O:15])[CH2:10][CH2:9]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:44][S:45]([NH2:48])(=[O:47])=[O:46].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>C1COCC1.O>[CH3:44][S:45]([NH:48][C:27]([C:26]1[CH:30]=[CH:31][C:23]([C:20]2[N:21]=[CH:22][C:17]([NH:16][C:14]([N:11]3[CH2:10][CH2:9][C:8](=[CH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:13][CH2:12]3)=[O:15])=[CH:18][CH:19]=2)=[CH:24][CH:25]=1)=[O:28])(=[O:47])=[O:46]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene2×HCID 66691817HCID 66691817, compound

Product 1

HCID 66692141HCID 66692141, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The compound (80 mg, 193 μmol) obtained in Example 28 was dissolved in THF (5 mL), and CDI (47 mg, 290 μmol) was added thereto, followed by stirring at 60° C. for 2 hours. Thereafter, methanesulfonamide (28 mg, 290 μmol) was added to the mixture, followed by stirring for 10 minutes, and diazabicycloundecene (hereinafter referred to as DBU) (51 μL, 347 μmol) was added thereto, followed by stirring at room temperature for 16 hours. Water was added to the resulting mixture, and after extraction with methanol:chloroform (1:6), the extract was washed with a saturated ammonium chloride aqueous solution and dried over anhydrous sodium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure flash column chromatography (silica gel; methanol:chloroform=1:6), thereby giving the title compound (30 mg, 32%) as a white solid.

Workup

  1. stirringby stirring for 10 minutes
  2. additionwas added
  3. stirringby stirring at room temperature for 16 hours
  4. extractionafter extraction with methanol:chloroform (1:6)
  5. washthe extract was washed with a saturated ammonium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter the desiccant was filtered off
  8. customthe residue obtained by evaporation under reduced pressure
  9. customwas purified

Sources & evidence

ORD record
ord-701ffce2628041f0a2049e0e8b32d45a
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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