1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → {6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynoylamino]-indol-1-yl}-acetic acid ethyl ester

HRID 751212Notes

Reaction equation

HRID 751212 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:15])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].[F:17][C:18]([F:34])([F:33])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH2:28][CH2:29][C:30](O)=[O:31])=[CH:22][CH:21]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:15][C:30](=[O:31])[CH2:29][CH2:28][C:27]#[C:26][C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:33])([F:34])[F:17])=[CH:21][CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16731704Ethyl 2-(6-amino-1H-indol-1-yl)acetateHCID 688226854-Pentynoic acid, 5-[4-(trifluoromethoxy)phenyl]-

Product 1

HCID 68821712{6-[5-(4-Trifluoromethoxy-phenyl)-pent-4-ynoylamino]-indol-1-yl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In analogy to the procedure described in example 8 c], (6-amino-indol-1-yl)-acetic acid ethyl ester (WO 2003041714 A1) was reacted with 5-(4-trifluoromethoxy-phenyl)-pent-4-ynoic acid in the presence of 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride and 4-(dimethylamino)pyridine to give the title compound as brown crystals.

Sources & evidence

ORD record
ord-00834225e95d4ba3ba6517c0b3e9d600
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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