Triethylamine → 7-Chloro-3-{[(6-chloro-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

HRID 1887851Notes

Reaction equation

HRID 1887851 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:21]([N:23]([CH3:25])[CH3:24])=[O:22].[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][N:28]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:24][N:23]([CH3:25])[C:21]([C:4]1[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6]2[C:11]([C:12](=[O:13])[C:3]=1[CH2:2][NH:1][C:31]([C:30]1[CH:29]=[N:28][C:27]([Cl:26])=[CH:35][CH:34]=1)=[O:32])=[CH:10][CH:9]=[C:8]([Cl:14])[CH:7]=2)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 712086753-(aminomethyl)-7-chloro-N,N-dimethyl-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxamide2×

Product 1

HCID 718111287-Chloro-3-{[(6-chloro-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(aminomethyl)-7-chloro-N,N-dimethyl-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxamide (intermediate C, 200 mg, 0.562 mmol), 6-chloronicotinoyl chloride (109 mg, 0.618 mmol), triethylamine (0.157 mL, 1.13 mmol) and methylene chloride (30 mL) was stirred at room temperature. The crude material was purified by flash chromatography (10% ethyl acetate in hexanes ramped to 70% ethyl acetate in hexanes) to give 7-chloro-3-{[(6-chloro-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide.

Workup

  1. customThe crude material was purified by flash chromatography (10% ethyl acetate in hexanes ramped to 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e20971d3d749400586bc9f5c8124800c
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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