4-Pyridinemethanamine → N-(pyridin-4-ylmethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide

HRID 1970000Notes

Reaction equation

HRID 1970000 reaction equation
[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[C:14]([C:15]([OH:17])=O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1>>[N:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:15]([C:14]2[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[NH:3][C:2](=[O:1])[C:11]=3[NH:12][CH:13]=2)=[O:17])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 773174-PyridinemethanamineHCID 120650844-oxo-3H,4H,5H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 15605218N-(pyridin-4-ylmethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamideYield 44%

Procedure

This compound is prepared according to synthesis 79 from 75 mg (0.33 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 75) and 37 μL (0.36 mmol) of pyridin-4-ylmethylamine. The precipitate that forms during the reaction is filtered then washed with dimethylformamide and diethyl ether to give 46 mg (44%) of N-(pyridin-4-ylmethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. filtrationis filtered
  3. washthen washed with dimethylformamide and diethyl ether

Sources & evidence

ORD record
ord-51800a6f59994ab18ce41147d8fe6f7d
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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