HCID 15521016, compound → HCID 54326711, compound

HRID 651095Notes

Reaction equation

HRID 651095 reaction equation
O.[NH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]([NH:21][CH:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23](O)=[O:24])=[O:20])=[CH:13]2>C(OCC)(=O)C>[CH2:26]([CH:22]([NH:21][C:19]([C:14]1[NH:15][C:16]2[C:12]([CH:13]=1)=[CH:11][C:10]([Cl:9])=[CH:18][CH:17]=2)=[O:20])[C:23](=[O:24])[N:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 15521016HCID 15521016, compoundHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 54326711HCID 54326711, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Piperidone monohydrate (2.0 mmol) and 2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (1.0 mmol) were coupled according to procedure A (0-25° C. reaction temperature) substituting the following workup: the reaction mixture was diluted with ethyl acetate, the resulting solution washed with 2 N NaOH and 2 N HCl, the suspension filtered and the solids dried: Yield 111 mg, 26%; HPLC (60/40) 8.88 minutes (92%); PBMS 424/426 (MH+, 100%); mp 258-261° C.; PBMS 424/426 (MH+, 100%);

Workup

  1. washthe resulting solution washed with 2 N NaOH and 2 N HCl
  2. filtrationthe suspension filtered
  3. customthe solids dried
  4. customHPLC (60/40) 8.88 minutes (92%)

Sources & evidence

ORD record
ord-174bf9b05d5044e2a4901e60d27c7b37
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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