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

HRID 2277398Notes

Reaction equation

HRID 2277398 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:25])[CH:3]=1.[CH3:26][N:27]1[C:31]([CH3:32])=[C:30]([C:33](O)=[O:34])[C:29](=[O:36])[N:28]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[F:25][C:4]1[CH:3]=[C:2]([NH:1][C:33]([C:30]2[C:29](=[O:36])[N:28]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:27]([CH3:26])[C:31]=2[CH3:32])=[O:34])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 681938392-((4-(4-Amino-2-fluorophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol

Product 1

HCID 68194384N-(3-fluoro-4-((7-((1-hydroxy-2-methylpropan-2-yl)oxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((4-(4-amino-2-fluorophenoxy)quinolin-7-yl)oxy)-2-methylpropan-1-ol (2.84 g, 8.3 mmol) in DCM (30 mL) was added 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (1.97 g, 8.4 mmol), EDCI (1.92 g, 10.0 mmol) and HOAT (0.23 g, 1.7 mmol). The reaction mixture was stirred at reflux for 4 hours and then concentrated in vacuo. The residue was stirred in 95% EtOH (50 mL)/water (30 mL), and then filtered to give the title compound as a light yellow solid (3.52 g, 76.2%).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated in vacuo
  3. stirringThe residue was stirred in 95% EtOH (50 mL)/water (30 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-6d947e8ac05246f0a32f561ab2082eda
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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