1,1'-Carbonyldiimidazole → HCID 22709915, compound

HRID 352893Notes

Reaction equation

HRID 352893 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:27][C:28](O)=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:43][S:44]([NH2:47])(=[O:46])=[O:45].C1CCN2C(=NCCC2)CC1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:15])=[O:16])[CH2:10][CH:9]1[CH2:27][C:28](=[O:29])[NH:47][S:44]([CH3:43])(=[O:46])=[O:45])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22709504HCID 22709504, compound

Product 1

HCID 22709915HCID 22709915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (10 ml) was dissolved 1-tert-butoxycarbonyl-2-carboxymethyl-4-[(5-chloroindol-2-yl)sulfonyl]piperazine (1.00 g), followed by the addition of carbonyldiimidazole (1.06 g). The resulting mixture was heated overnight under reflux. After cooling to room temperature, methanesulfonamide (415 mg) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.64 ml) were added, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. Dichloromethane was added to the residue and the resulting mixture was washed successively with 1N hydrochloric acid, and saturated aqueous NaCl solution. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (Φ3.0×10.0 cm, dichloromethane:methanol=100:1), whereby the title compound (518 mg, 44%) was obtained as colorless foam.

Workup

  1. temperatureThe resulting mixture was heated overnight
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionDichloromethane was added to the residue
  5. washthe resulting mixture was washed successively with 1N hydrochloric acid, and saturated aqueous NaCl solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by chromatography on a silica gel column (Φ3.0×10.0 cm, dichloromethane:methanol=100:1), whereby the title compound (518 mg, 44%)
  10. customwas obtained as colorless foam

Sources & evidence

ORD record
ord-097fc1ec2a9246de9f95d04f5a065b82
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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