1,1'-Carbonyldiimidazole → HCID 10162497, compound

HRID 1745907Notes

Reaction equation

HRID 1745907 reaction equation
C(OC([NH:8][CH2:9][C:10](O)=[O:11])=O)(C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:25][O:26][CH2:27][CH2:28][O:29][C:30]1[CH:55]=[CH:54][C:33]2[N:34]([C:37]3[CH:46]=[CH:45][C:44]4[C:39](=[C:40]([N:47]5[CH2:52][CH2:51][CH:50]([NH2:53])[CH2:49][CH2:48]5)[CH:41]=[CH:42][CH:43]=4)[N:38]=3)[CH:35]=[N:36][C:32]=2[CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:8][CH2:9][C:10]([NH:53][CH:50]1[CH2:49][CH2:48][N:47]([C:40]2[CH:41]=[CH:42][CH:43]=[C:44]3[C:39]=2[N:38]=[C:37]([N:34]2[C:33]4[CH:54]=[CH:55][C:30]([O:29][CH2:28][CH2:27][O:26][CH3:25])=[CH:31][C:32]=4[N:36]=[CH:35]2)[CH:46]=[CH:45]3)[CH2:52][CH2:51]1)=[O:11]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 10158940CP-673451

Product 1

HCID 10162497HCID 10162497, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(tert-butoxycarbonyl)glycine (105 mg, 0.600 mMol) was dissolved in 3 mL of DCM under an atmosphere of dry N2. To this mixture was added 1,1′-carbonyldiimidazole (100 mg, 0.61 mMol) and the reaction mixture was stirred at ambient temperature for 30 minutes. To this solution was then added 4-dimethylaminopyridine (8.0 mg, 0.065 mMol) and 1-{2-[5-(2-methoxy-ethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine 33 (170 mg, 0.408 mMol). The reaction mixture was subsequently stirred overnight at ambient temperature. The reaction mixture was then partitioned between DCM and saturated aqueous NaHCO3. The organic layer was saved and washed again with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to give a yellow foam. The residue was chromatographed on flash silica gel eluting with MeOH/DCM (397) to give 182 mg of a yellow residue. The residue was dissolved in 0.5 ml of TFA and stirred at ambient temperature for 30 minutes under an atmosphere of dry N2. The reaction mixture was subsequently concentrated under vacuum and then partitioned between 0.1 N aqueous NaOH. The organic layer was saved and washed again with 0.1 N aqueous NaOH, dried over Na2SO4, filtered and concentrated under vacuum to give a yellow foam. The foam was chromatographed on flash silica gel eluting with MeOH/DCM (595) to give 75 mg of the title compound as 54 a yellow solid.

Workup

  1. waitThe reaction mixture was subsequently stirred overnight at ambient temperature
  2. customThe reaction mixture was then partitioned between DCM and saturated aqueous NaHCO3
  3. washwashed again with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give a yellow foam
  8. customThe residue was chromatographed on flash silica gel eluting with MeOH/DCM (397)

Sources & evidence

ORD record
ord-4e4b938f0a9c4a1cabbb5087cf07f66d
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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