Diethylamine → HCID 15521017, compound

HRID 651090Notes

Reaction equation

HRID 651090 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([NH:18][CH:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:20](O)=[O:21])=[O:17])=[CH:10]2>C(Cl)(Cl)Cl.ClCCl>[CH2:1]([N:3]([CH2:4][CH3:5])[C:20]([CH:19]([NH:18][C:16]([C:11]1[NH:12][C:13]2[C:9]([CH:10]=1)=[CH:8][C:7]([Cl:6])=[CH:15][CH:14]=2)=[O:17])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 15521017HCID 15521017, compound

Reagents, catalysts & solvents 1

HCID 18399249Chloroform dichloromethaneSolvent

Procedure

Diethylamine(1.2 mmol) and 2-[(5-chloro-1H-indol-2-carbonyl)-amino]3-phenyl-propionic acid (0.6 mmol) were coupled according to procedure A (0-25° C. for 5 days) substituting the following workup: the crude product was suspended in 1:1 chloroform/dichloromethane, sonicated, filtered to remove solids, concentrated, and the residue purified by column chromatography on silica gel eluted with 10, 20 and 30% ethyl acetate in hexanes: Yield 14 mg, 6%; HPLC (60/40) 8.88 minutes (98%); PBMS 398/400 (MH+, 100%);

Workup

  1. customwere coupled according to procedure A (0-25° C. for 5 days)
  2. customsonicated
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationconcentrated
  6. customthe residue purified by column chromatography on silica gel
  7. washeluted with 10, 20 and 30% ethyl acetate in hexanes
  8. customHPLC (60/40) 8.88 minutes (98%)

Sources & evidence

ORD record
ord-9dd3f2faa0ad44c491687ad6bff32635
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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