4-Methylmorpholine → 1,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-5-propyl-1H-imidazol-2-yl]-1H-indole-1-carboxylate

HRID 1246217

Reaction equation

HRID 1246217 reaction equation
O.ON1C2C=CC=CC=2N=N1.[C:12]([C:15]1[N:16]=[C:17]([CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:18][C:19]=1[CH2:20][CH2:21][CH3:22])(O)=[O:13].Cl.[CH3:40][O:41][C:42](=[O:45])[CH2:43][NH2:44].Cl.C(C(NCCCN(C)C)=N)C.CN1CCOCC1>C(Cl)Cl.C1COCC1>[CH3:40][O:41][C:42](=[O:45])[CH2:43][NH:44][C:12]([C:15]1[N:16]=[C:17]([CH:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]2[C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[NH:18][C:19]=1[CH2:20][CH2:21][CH3:22])=[O:13]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 122755Glycine methyl ester hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 219140991,1-dimethylethyl 2-(4-carboxy-5-propyl-1H-imidazol-2-yl)-2,3-dihydro-1H-indole-1-carboxylateHCID 178458058HCID 178458058, compound

Product 1

HCID 219141261,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-5-propyl-1H-imidazol-2-yl]-1H-indole-1-carboxylateYield 57.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxybenzotriazole hydrate (0.00158 mole) was added to a solution of compound 105 (0.00079 mole) in DCM (80 ml). Glycine methylester hydrochloride (0.00103 mole), N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3 propanediamine monohydrochloride (0.00103 mole) and 4-methylmorpholine (0.00103 mole) were added. THF (25 mm) was added. The reaction was stirred at room temperature for 3 days. The mixture was extracted with water. The organic phase was washed with saturated NaHCO3, 2N citric acid, saturated NaHCO3, dried over MgSO4, filtered, and concentrated, yielding 0.20 g of 1,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-5-propyl-1H-imidazol-2-yl]-1H-indole-1-carboxylate (compound 109).

Workup

  1. extractionThe mixture was extracted with water
  2. washThe organic phase was washed with saturated NaHCO3, 2N citric acid, saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71d88d037be34e7e867a7508428956b3
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Linked notes

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