Ethylmorpholine → 5-(4-Trifluoromethyl-phenyl)-pent-4-ynoic acid (1H-indol-6-ylmethyl)-amide

HRID 751228Notes

Reaction equation

HRID 751228 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:5][CH:4]=1.NC[CH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][NH:27]2)=[CH:23][CH:22]=1.O[N:31]1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.Cl.CN(C)CCCN=C=NCC>>[NH:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([CH2:20][NH:31][C:13](=[O:15])[CH2:12][CH2:11][C:10]#[C:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:16])=[CH:8][CH:7]=3)[CH:29]=2)[CH:25]=[CH:26]1

Participants

6

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 172211002-(1H-indol-6-yl)ethan-1-amineHCID 68824010HCID 68824010, compound

Product 1

HCID 860955295-(4-Trifluoromethyl-phenyl)-pent-4-ynoic acid (1H-indol-6-ylmethyl)-amide

Procedure

In analogy to the procedure described for example 13 a], 5-(4-trifluoromethyl-phenyl)-pent-4-ynoic acid was reacted with 6-aminoethyl-1H-indole in the presence of 1-hydroxybenzotriazole, 4-ethylmorpholine and 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride to give the title compound as colorless crystals.

Sources & evidence

ORD record
ord-beced779e0224c3ba3ae5545346f4028
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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