1-Hydroxybenzotriazole → N-[1-amino(3,5-dimethyl-1H-pyrazol-1-yl)methylene]-4-(2,4,6-trifluorophenyl)quinoline-6-carboxamide

HRID 533395Notes

Reaction equation

HRID 533395 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[N+]([O-])(O)=O.[CH3:49][C:50]1[CH:54]=[C:53]([CH3:55])[N:52]([C:56](=[NH:58])[NH2:57])[N:51]=1.CCN(C(C)C)C(C)C>O.CN(C=O)C>[NH2:58][C:56]([N:52]1[C:53]([CH3:55])=[CH:54][C:50]([CH3:49])=[N:51]1)=[N:57][C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[C:10]2[C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[F:9])=[O:21]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 677759694-(2,4,6-Trifluorophenyl)quinoline-6-carboxylic acid

Product 1

HCID 67774710N-[1-amino(3,5-dimethyl-1H-pyrazol-1-yl)methylene]-4-(2,4,6-trifluorophenyl)quinoline-6-carboxamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2,4,6-trifluorophenyl)quinoline-6-carboxylic acid (118 mg), WSC hydrochloride (112 mg), HOBt (37 mg), and DMF (4 mL) was stirred at room temperature for 5 minutes, and then 3,5-dimethyl-1H-pyrazole-1-carboximidamide nitrate (94 mg) and DIPEA (76 mg) were added thereto, followed by stirring for an additional 24 hours. The reaction mixture was diluted with water, and the precipitate was collected by filtration to obtain N-[1-amino(3,5-dimethyl-1H-pyrazol-1-yl)methylene]-4-(2,4,6-trifluorophenyl)quinoline-6-carboxamide (140 mg).

Workup

  1. stirringby stirring for an additional 24 hours
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-307778821b1a40cc925d19ba7f9edaed
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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