1-Propylethylenediamine → 5-Nitro-1H-indole-2-carboxylic acid (2-propylamino-ethyl)-amide

HRID 1829979

Reaction equation

HRID 1829979 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)=[O:8])[CH3:2].[CH2:21](OC(C1NC2C(C=1)=CC([N+]([O-])=O)=CC=2)=O)C.C(NCCN)CC>>[CH2:1]([NH:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH3:21]

Participants

4

Reactant 3

HCID 660731-PropylethylenediamineHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylateHCID 85801380N-[2-(ethylamino)ethyl]-5-nitro-1H-indole-2-carboxamide

Product 1

HCID 858013855-Nitro-1H-indole-2-carboxylic acid (2-propylamino-ethyl)-amideYield 85%

Procedure

A similar procedure as described for preparation of 77 from 5-nitro-2-indolecarboxylic acid ethyl ester (0.8 g, 3.41 mmol) and N-propylethylenediamine (2 ml) gave a brown solid (0.84 g, 85%). ESI MS: 291.13 (M+H+). 1H NMR (DMSO-d6) δ 8.68 (d, 1H), 8.04 (d, 1H), 7.55 (d, 1H), 7.37 (s, 1H), 3.35 (m, 3H), 2.68 (q, 2H), 2.49 9 (q, 2H), 1.40 (tt, 2H), 0.84 (t, 3H).

Sources & evidence

ORD record
ord-9f46ccf9e1274fdd886f09938b88b301
Source dataset
uspto-grants-2006_06
Patent number
US07064218B2

Linked notes

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