Methyl 3-(prop-2-enamido)propanoate → 8-[2-(2-methoxycarbonyl-ethylcarbamoyl)-vinyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1969990Notes

Reaction equation

HRID 1969990 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[NH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[CH:3]=1.[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17].[C:21]([NH:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])(=[O:24])[CH:22]=[CH2:23]>ClCCl>[CH3:31][O:30][C:28]([CH2:27][CH2:26][NH:25][C:21]([CH:22]=[CH:23][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[NH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[CH:3]=1)=[O:24])=[O:29].[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17]

Participants

4

Reactant 2

HCID 15609289Methyl 3-(prop-2-enamido)propanoateHCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275168-[2-(2-methoxycarbonyl-ethylcarbamoyl)-vinyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound is prepared according to synthesis 68, from 70 mg (0.21 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 71) and 36 mg (0.23 mmol) of methyl 3-acryloylamino-propionate. After trituration in dichloromethane, 10 mg (12%) of 8-[2-(2-methoxycarbonyl-ethylcarbamoyl)-vinyl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a light brown solid.

Workup

  1. customThis compound is prepared

Sources & evidence

ORD record
ord-8f295210adad4dbf9cea9924011b7855
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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