Ethylmorpholine → 2-(1H-Indol-6-yl)-N-methyl-N-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-acetamide

HRID 751234Notes

Reaction equation

HRID 751234 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]([OH:13])=O)[CH:8]=2)[CH:3]=[CH:2]1.[CH3:14][NH:15][CH2:16][C:17]#[C:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.Cl.CN(C)CCCN=C=NCC>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]([N:15]([CH3:14])[CH2:16][C:17]#[C:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:23][CH:24]=3)=[O:13])[CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 148825031H-Indole-6-acetic acidHCID 688239102-Propyn-1-amine, N-methyl-3-[4-(trifluoromethoxy)phenyl]-

Product 1

HCID 688217222-(1H-Indol-6-yl)-N-methyl-N-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-acetamide

Procedure

In analogy to the procedure described for example 13 a], (1H-indol-6-yl)-acetic acid (U.S. Pat. No. 4,894,386 A) was reacted with methyl-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-amine in the presence of 1-hydroxybenzotriazole, 4-ethylmorpholine and 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride to give the title compound as orange oil.

Sources & evidence

ORD record
ord-4cc0068907b6456aa7008e58d55fe240
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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