1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-((7-(2-hydroxyethoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2277389Notes

Reaction equation

HRID 2277389 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][OH:20])=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:23][N:24]1[C:28]([CH3:29])=[C:27]([C:30](O)=[O:31])[C:26](=[O:33])[N:25]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O>[OH:20][CH2:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:30]([C:27]4[C:26](=[O:33])[N:25]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:24]([CH3:23])[C:28]=4[CH3:29])=[O:31])=[CH:22][CH:21]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 681938652-((4-(4-Aminophenoxy)quinolin-7-yl)oxy)ethanol

Product 1

HCID 60172981N-(4-((7-(2-hydroxyethoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((4-(4-aminophenoxy)quinolin-7-yl)oxy)ethanol (0.14 g, 0.5 mmol), 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (0.11 g, 0.51 mmol) in DCM (1.5 mL) was added HOAT (0.014 g, 0.1 mmol), and EDCI (0.11 g, 0.6 mmol). The reaction was refluxed for 3 hours. The cooled mixture was diluted with water (30 mL) and filtered. The solid was collected and stirred in a mixture of EtOAc (3 mL) and water (3 mL) overnight. The solid was collected by filtration and dried in vacuo at 50° C. for 9 hours to afford the title compound as a gray-white solid (180 mg, 74.7%).

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. filtrationfiltered
  3. customThe solid was collected
  4. filtrationThe solid was collected by filtration
  5. customdried in vacuo at 50° C. for 9 hours

Sources & evidence

ORD record
ord-8ddae10055ee498ca81b02402e230801
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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