N-(3-Aminopropyl)morpholine → HCID 54546641, compound

HRID 651098Notes

Reaction equation

HRID 651098 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([NH:23][CH:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:25](O)=[O:26])=[O:22])=[CH:15]2>C(OCC)(=O)C>[N:5]1([CH2:4][CH2:3][CH2:2][NH:1][C:25]([CH:24]([NH:23][C:21]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([Cl:11])=[CH:20][CH:19]=3)=[O:22])[CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 54546641HCID 54546641, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(3Aminopropyl)morpholine (0.34 mmol) and 2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (0.30 mmol) were coupled according to Procedure A (0-25° C. reaction temperature) substituting the following workup: the reaction was diluted with ethyl acetate, the resulting solution washed three times with 2 N NaOH and once with brine, dried over Na2SO4, and concentrated. The residue was stirred under ether for 1 hour, the solid filtered and dried: Yield 125 mg, 87%; HPLC (60/40) 2.85 minutes (98%); PBMS 469/471 (MH+, 100/90%);

Workup

  1. washthe resulting solution washed three times with 2 N NaOH
  2. dry with materialonce with brine, dried over Na2SO4
  3. concentrationconcentrated
  4. filtrationthe solid filtered
  5. customdried
  6. customHPLC (60/40) 2.85 minutes (98%)

Sources & evidence

ORD record
ord-3ae9cf21b4214fedae0b762d8adfc84d
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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