Tryptamine → N-[2-(1H-indol-3-yl)-ethyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide

HRID 1969998Notes

Reaction equation

HRID 1969998 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.[NH2:18][CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1>C(OCC)C>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH2:20][CH2:19][NH:18][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:22]1

Participants

4

Reactant 2

HCID 1150TryptamineHCID 120650844-oxo-3H,4H,5H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 15605219N-[2-(1H-indol-3-yl)-ethyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 58 mg (0.36 mmol) of tryptamine. After trituration in diethyl ether, 48 mg (40%) of N-[2-(1H-indol-3-yl)-ethyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide is obtained in the form of a light brown solid.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-e3f2452d7969416ebbd738b8b6163904
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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