Imidazole → HCID 23110281, compound

HRID 2356946Notes

Reaction equation

HRID 2356946 reaction equation
N1([C:6](N2C=CN=C2)=[O:7])C=CN=C1.N1C=CN=C1.[CH2:18]([O:20][CH:21]([O:33][CH2:34][CH3:35])[CH2:22][O:23][C:24]1[CH:25]=[C:26]([NH2:32])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH3:19].CO[C:38](=[O:54])[C:39]([CH3:53])([NH:41][CH2:42][C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:46]=[CH:45][CH:44]=1)[CH3:40]>O1CCCC1>[CH2:34]([O:33][CH:21]([O:20][CH2:18][CH3:19])[CH2:22][O:23][C:24]1[CH:25]=[C:26]([N:32]2[C:38](=[O:54])[C:39]([CH3:40])([CH3:53])[N:41]([CH2:42][C:43]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[N:46]=[CH:45][CH:44]=3)[C:6]2=[O:7])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH3:35]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 23110289HCID 23110289, compoundHCID 59694308HCID 59694308, compound

Product 1

HCID 23110281HCID 23110281, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 317 mg di-imidazol-1-yl-methanone and 20 mg imidazole in 4 ml tetrahydrofuran a solution of 500 mg 3-(2,2-diethoxy-ethoxy)-4-methoxy-phenylamine in 2 ml tetrahydrofuran was slowly added at 0° C. After stirring at 0° C. for 1 hour 505 mg 2-methyl-2-[(quinolin-4-ylmethyl)-amino]-propionic acid methyl ester were added and the reaction mixture was allowed to warm up to room temperature. After 2 hours stirring at room temperature the solution was heated for 2 hours at 70° C. After cooling to room temperature the solvent of the mixture was removed under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid). Lyophilization of the solution yielded a white solid. Yield: 300 mg

Workup

  1. additionwere added
  2. temperaturewas heated for 2 hours at 70° C
  3. temperatureAfter cooling to room temperature the solvent of the mixture
  4. customwas removed under reduced pressure
  5. customthe residue was purified by preparative HPLC (
  6. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid)
  7. customLyophilization of the solution yielded a white solid

Sources & evidence

ORD record
ord-d6208bb8fe484be6a54d9580c237b667
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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