N-(1-Naphthyl)ethylenediamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(naphthalen-1-ylamino)ethyl]amide

HRID 751687Notes

Reaction equation

HRID 751687 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:5]2=[CH:6][N:7]=1.[C:14]1([NH:24][CH2:25][CH2:26][NH2:27])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>>[C:14]1([NH:24][CH2:25][CH2:26][NH:27][C:11]([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[CH:10]=2)=[O:13])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 15107N-(1-Naphthyl)ethylenediamineHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 113944315-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(naphthalen-1-ylamino)ethyl]amide

Procedure

The title compound was prepared as outlined in EXAMPLE 1 from 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 18) and 2-(naphthalen-1-ylamino)ethylamine. The product was purified by mass directed purification to give the title compound as a brown solid. δH (CD3OD): 3.55 (2H, t), 3.80 (2H, t), 6.68 (1H, d), 7.04 (1H, s), 7.14 (1H, d), 7.28 (1H, t), 7.36–7.42 (2H, m), 7.65 (1H, s), 7.70–7.74 (1H, m), 7.98–8.02 (1H, m), 8.58 (1H, s); m/z (ES+)=365 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customThe product was purified by mass
  3. custompurification

Sources & evidence

ORD record
ord-8d1f2e0f52964790ab6db3b7f8afb792
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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