1,1'-Carbonyldiimidazole → HCID 22478758, compound

HRID 252775Notes

Reaction equation

HRID 252775 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:38])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([OH:37])[CH2:23][NH:24][C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)=[CH:18][CH:17]=1)(C)(C)C.[C:40](N1C=CN=C1)(N1C=CN=C1)=[O:41]>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:38])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[O:37][C:40](=[O:41])[N:24]([C:25]3[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=3)[CH2:23]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 20786183HCID 20786183, compound

Product 1

HCID 22478758HCID 22478758, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 295 (130 mg, 0.242 mmol) in DCM (2 mL) was added 1,1′-carbonyldiimidazole (47 mg, 0.29 mmol) and the mixture was stirred at room temperature for 16 h. DCM was removed under reduced pressure, AcOEt and a solution of sat. NH4Cl were added and the phases were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography on silica gel (Hexane/AcOEt: 30/70) to afford the desired compound (80 mg, 0.14 mmol, 58% yield). 1H NMR (DMSO) δ (ppm): 9.39 (s, 1H), 8.04 (d, J=8.1 Hz, 2H), 7.84 (d, J=7.5 Hz, 1H), 7.52 (d, J=8.1 Hz, 2H), 7.26-7.12 (m, 3H), 6.86-6.74 (m, 3H), 5.70 (t, J=8.4 Hz, 1H), 4.24 (t, J=8.7 Hz, 1H), 3.97-3.87 (m, 1H), 3.87 (s, 6H), 3.82 (s, 3H), 1.52 (s, 9H).

Workup

  1. customDCM was removed under reduced pressure, AcOEt
  2. additiona solution of sat. NH4Cl were added
  3. customthe phases were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash chromatography on silica gel (Hexane/AcOEt: 30/70)

Sources & evidence

ORD record
ord-948a10d26966407f8c88d6f6409ef286
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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