4-Methylmorpholine → HCID 178501649, compound

HRID 1246215

Reaction equation

HRID 1246215 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH2:17].CN1CCOCC1.Cl.C(C(NCCCN(C)C)=N)C.[C:38]([C:41]1[N:42]=[C:43]([CH:46]2[CH2:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]2[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[NH:44][CH:45]=1)(O)=[O:39]>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:18])[CH2:16][NH:17][C:38]([C:41]1[N:42]=[C:43]([CH:46]2[CH2:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]2[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[NH:44][CH:45]=1)=[O:39]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 122755Glycine methyl ester hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178451416HCID 178451416, compoundHCID 178458058HCID 178458058, compound

Product 1

HCID 178501649HCID 178501649, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Hydroxybenzotriazole hydrate (0.00036 mole), glycine methylester, hydrochloride (0.00047 mole), 4-methylmorpholine (0.00055 mole), and N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine monohydrochloride (0.00047 mole) were added to compound 117 (0.00036 mole) dissolved in DCM (30 ml) at 0° C. The mixture was allowed to warm to room temperature under nitrogen, and stirred overnight. The mixture was extracted with water, saturated NaHCO3, 2N citric acid, then saturated NaHCO3, dried, filtered, and concentrated, yielding 0.100 g (69%) of 1,1-dimethylethyl 2,3-dihydro-2-[4-[[(2-methoxy-2-oxoethyl)amino]carbonyl]-1H-imidazol-2-yl]-1H-indole-1-carboxylate (compound 118).

Workup

  1. extractionThe mixture was extracted with water, saturated NaHCO3, 2N citric acid
  2. dry with materialsaturated NaHCO3, dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1838593a875e4541ab89b8c4dbf1848b
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Linked notes

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