4-Methylmorpholine → HCID 140381235, compound

HRID 1682669Notes

Reaction equation

HRID 1682669 reaction equation
CN1CCOCC1.Cl.Cl.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:13][CH2:12]1.[CH3:24][O:25][C:26]([NH:28][C:29]([C:31]1[CH:32]=[CH:33][C:34]2[O:38][C:37]([C:39]([O-])=[O:40])=[CH:36][C:35]=2[CH:42]=1)=[NH:30])=[O:27].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>O.CN(C)C=O>[CH3:24][O:25][C:26]([NH:28][C:29]([C:31]1[CH:32]=[CH:33][C:34]2[O:38][C:37]([C:39]([NH:10][CH:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:16]3)=[O:40])=[CH:36][C:35]=2[CH:42]=1)=[NH:30])=[O:27]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18919424HCID 18919424, compoundHCID 178502508HCID 178502508, compound

Product 1

HCID 140381235HCID 140381235, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

N,N-Dimethylformamide (14 ml) and N-methylmorpholine (0.57 ml, 5.20 mmol) were added to ethyl 3-(4-aminopiperidino)propionate dihydrochloride (567 mg, 2.08 mmol) and the mixture was stirred at 60° C. for 20 minutes under a nitrogen atmosphere. This solution was added to a mixture of 5-(methoxycarbonylamidino)-2-benzofurancarboxylate acid (364 mg, 1.39 mmol), 1-hydroxy-1H-benzotriazole (207 mg, 1.54 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (294 mg, 1.54 mmol) added to N,N-dimethylformamide (15 ml). The mixture was stirred at room temperature for 18 hours. Water (100 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure. The residue was purified by column chromatography (chloroform/methanol=10/1) to give 338 mg of compound (187) as a yellow solid (55%).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration, low boiling matters
  6. distillationwere distilled away from the filtrate under reduced pressure
  7. customThe residue was purified by column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-0da7dadea9c840fa8f0e266c255b51b5
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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