Morpholine → HCID 54244785, compound

HRID 651093Notes

Reaction equation

HRID 651093 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([NH:19][CH:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21](O)=[O:22])=[O:18])=[CH:11]2>>[CH2:24]([CH:20]([NH:19][C:17]([C:12]1[NH:13][C:14]2[C:10]([CH:11]=1)=[CH:9][C:8]([Cl:7])=[CH:16][CH:15]=2)=[O:18])[C:21]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 54244785HCID 54244785, compound

Procedure

Morpholine (0.33 mmol) and 2-[(5chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (0.30 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 48 hour reaction time). The crude product was chromatographed on silica gel eluted with 1:1 ethyl acetate/hexanes, the desired fractions concentrated, the residue dissolved in chloroform and methanol and the resulting solution stirred 18 hours with approx. 128 mg dimethylaminopyridine-polystyrene resin (Fluka Chemical Co.). The solution was filtered, concentrated and the residue triturated with ether: Yield, 51%; HPLC (60/40) 5.92 min (98%);

Workup

  1. customThe crude product was chromatographed on silica gel
  2. washeluted with 1:1 ethyl acetate/hexanes
  3. concentrationthe desired fractions concentrated
  4. dissolutionthe residue dissolved in chloroform
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customthe residue triturated with ether
  8. customYield

Sources & evidence

ORD record
ord-d2276b037c004020b993f29adf261691
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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