Thiopheneethanamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-thiophen-2-ylethyl)amide

HRID 751680Notes

Reaction equation

HRID 751680 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.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][CH2:20][NH2:21]>>[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][CH2:20][NH:21][C:11]([C:9]1[NH:8][C:5]2=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=1)=[O:13]

Participants

3

Reactant 2

HCID 116521ThiopheneethanamineHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 113357585-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-thiophen-2-ylethyl)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-thiophen-2-ylethylamine. The product was purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97) to give the title compound as a yellow solid. δH (CD3OD): 3.16 (2H, t), 3.65 (2H, t), 6.89–6.94 (2H, m), 7.03 (1H, s), 7.20 (1H, d), 7.66 (1H, s), 8.57 (1H, s); m/z (ES+)=306 [M+H]+.

Workup

  1. customThe title compound was prepared
  2. customThe product was purified by chromatography on silica gel eluting with methanol/dichloromethane (3:97)

Sources & evidence

ORD record
ord-16c0d40da0014a58b51b6dd4a52e5e98
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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