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

HRID 1872115Notes

Reaction equation

HRID 1872115 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-(3-Aminopropyl)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 2N 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 2N 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-a9721815760b4410a6bd55ce1ae3446d
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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