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

HRID 1786835Notes

Reaction equation

HRID 1786835 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=O)=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19])#[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.[CH3:73][O:74][C:75]1[CH:86]=[C:85]2[C:78]([NH:79][CH:80]=[C:81]2[CH2:82][CH2:83][NH2:84])=[CH:77][CH:76]=1>CN(C=O)C>[CH3:73][O:74][C:75]1[CH:86]=[C:85]2[C:78](=[CH:77][CH:76]=1)[NH:79][CH:80]=[C:81]2[CH2:82][CH2:83][NH:84][C:9](=[O:11])[CH:8]([O:7][C:6]1[CH:16]=[CH:17][C:3]([C:1]#[N:2])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:5]=1)[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 61981H-Indole-3-ethanamine, 5-methoxy-, hydrochloride (1:?)HCID 79724-MethylmorpholineHCID 18366554HCID 18366554, compoundHCID 57598540HCID 57598540, compoundHCID 866308461-(Dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

Product 1

HCID 575984702-(4-Cyano-3-trifluoromethyl-phenoxy)-4-methyl-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 (0.83 mmol) of 2-(4-cyano-3-trifluoromethyl-phenoxy)-4-methyl-pentanoic acid in dimethylformamdie “DMF” (15 mL) were added 0.14 gm (1.04 mmol) of 1-Hydroxy-benzotriazole HOBT, 0.2 gm (1.04 mmol) of (3-(dimethylamino)propyl)ethylcarbodiimide EDCl, 0.23 gm (2.28 mmol) N-methyl morpholine, and approximately 234 mg of 5-methoxytryptamine hydrochloride (1.04 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-3169ad53d41a41a3a8c9ea8043dc34d8
Source dataset
uspto-grants-2009_03
Patent number
US07507860B2

Reaction notes

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