Methanol → HCID 54452286, compound

HRID 1872111Notes

Reaction equation

HRID 1872111 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[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.CO>C(Cl)(Cl)Cl>[CH2:1]([NH: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])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 8007ButylamineHCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 54452286HCID 54452286, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

n-Butyl amine (0.66 mmol) and 2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (0.60 mmol) were coupled according to procedure A (0-25° C. reaction temperature). The crude product was dissolved in chloroform and methanol and the resulting solution stirred 18 hours with 50 mg dimethylaminopyridine-polystyrene resin (Fluka Chemical Co.), the solution filtered, concentrated and the solids triturated with ether: Yield 83%; HPLC (60/40) 8.88 minutes (92%); mp 192-193° C.; TSPMS 398/400 (MH+,100%);

Workup

  1. filtrationthe solution filtered
  2. concentrationconcentrated
  3. customthe solids triturated with ether
  4. customHPLC (60/40) 8.88 minutes (92%)

Sources & evidence

ORD record
ord-d760d840dd284c10b2d2540b1bb21df6
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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