5-Methoxytryptamine → N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-3-(4-trifluoromethyl-phenyl)-propionamide

HRID 563916Notes

Reaction equation

HRID 563916 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[F:15][C:16]([F:29])([F:28])[C:17]1[CH:27]=[CH:26][C:20]([CH2:21][CH2:22][C:23](O)=[O:24])=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6](=[CH:5][CH:4]=1)[NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][C:23](=[O:24])[CH2:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([C:16]([F:28])([F:29])[F:15])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 18335-MethoxytryptamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 35887363-(4-(Trifluoromethyl)phenyl)propionic Acid

Product 1

HCID 59820000N-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-3-(4-trifluoromethyl-phenyl)-propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.3 g (1.57 mmol) 5-methoxytryptamine, 0.34 g (1.57 mmol) 4-(trifluoromethyl)hydrocinnamic acid (commercially available), 0.6 g (1.8 mmol) TBTU and 0.6 g (4.6 mmol) DIPEA in 6 mL DMF was shaken for 3 h at room temperature. 50 mL water was added and the mixture was extracted with DCM. The combined organic phases were washed with water, dried with MgSO4 and evaporated to dryness to yield the title compound which was used without further purification in the consecutive step.

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organic phases were washed with water
  3. dry with materialdried with MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-66c1d60f20694234ab7031c3f9fbe638
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

Loading…