1H-Indole-3-ethanamine, 5-methoxy-, hydrochloride (1:?) → 2-(4-Cyano-3-trifluoromethyl-phenoxy)-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide

HRID 1786834Notes

Reaction equation

HRID 1786834 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH2:12][CH2:13][CH3:14])[C:9]([OH:11])=O)=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18])#[N:2].ON1C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1.CN(C)CCCN=C=NCC.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1.Cl.[CH3:72][O:73][C:74]1[CH:85]=[C:84]2[C:77]([NH:78][CH:79]=[C:80]2[CH2:81][CH2:82][NH2:83])=[CH:76][CH:75]=1>CN(C=O)C>[CH3:72][O:73][C:74]1[CH:85]=[C:84]2[C:77](=[CH:76][CH:75]=1)[NH:78][CH:79]=[C:80]2[CH2:81][CH2:82][NH:83][C:9](=[O:11])[CH:8]([O:7][C:6]1[CH:15]=[CH:16][C:3]([C:1]#[N:2])=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:5]=1)[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 5

HCID 61981H-Indole-3-ethanamine, 5-methoxy-, hydrochloride (1:?)HCID 79724-MethylmorpholineHCID 183665541-hydroxybenzotriazole HOBTHCID 689255602-(4-Cyano-3-trifluoromethyl-phenoxy)-pentanoic acidHCID 866308461-(Dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

Product 1

HCID 575985482-(4-Cyano-3-trifluoromethyl-phenoxy)-pentanoic acid [2-(5-methoxy-1H-indol-3-yl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was prepared in the following manner. To 0.25 gm (0.87 mmol) of 2-(4-cyano-3-trifluoromethyl-phenoxy)-pentanoic acid in dimethylformamdie “DMF” (15 mL) were added 0.14 gm (1.09 mmol) of 1-Hydroxy-benzotriazole HOBT, 0.2 gm (1.09 mmol) of (3-(dimethylamino)propyl)ethylcarbodiimide EDCl, 0.23 gm (2.39 mmol) N-methyl morpholine, and approximately 246 mg of 5-methoxytryptamine hydrochloride (1.09 mmol). The resultant mixtures were stirred at room temperature for approximately 18 hours. The reactions were quenched with sodium bicarbonate (20 mL) and extracted with ethyl acetate (3 times 20 mL). The solvent was removed in vacuo to obtain oils that were then purified by HPLC.

Workup

  1. customThe compound was prepared in the following manner
  2. customThe reactions were quenched with sodium bicarbonate (20 mL)
  3. extractionextracted with ethyl acetate (3 times 20 mL)
  4. customThe solvent was removed in vacuo
  5. customto obtain oils that
  6. customwere then purified by HPLC

Sources & evidence

ORD record
ord-2703c2149ecf449b8647f8df81a3ed14
Source dataset
uspto-grants-2009_03
Patent number
US07507860B2

Reaction notes

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