1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-((7-hydroxy-6-methoxyquinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2277406Notes

Reaction equation

[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]1[C:27]([CH3:28])=[C:26]([C:29](O)=[O:30])[C:25](=[O:32])[N:24]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.O>[OH:19][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:20]=[CH:21][C:2]([NH:1][C:29]([C:26]4[C:25](=[O:32])[N:24]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:23]([CH3:22])[C:27]=4[CH3:28])=[O:30])=[CH:3][CH:4]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][C:14]=1[O:17][CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(4-aminophenoxy)-6-methoxyquinolin-7-ol (3.61 g, 12.8 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.85 g, 12.27 mmol) in DMF (50 mL) was added EDCI (2.81 g, 14.66 mmol) and HOAT (0.33 g, 2.4 mmol). The reaction was stirred at 60° C. for 10 hours, cooled to room temperature and diluted with H2O (200 mL). The solid was collected by filtration and dried in vacuo at 60° C. overnight to give the title compound as a white solid (5.7 g, 89.9%).

Workup

temperaturecooled to room temperature
filtrationThe solid was collected by filtration
customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record: ord-0c68dcc7436349f6bb0aca6e57a8baea
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

Loading…