1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-((2-aminopyridin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-c arboxamide

HRID 870443Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[CH3:10][N:11]1[C:15]([CH3:16])=[C:14]([C:17]([OH:19])=O)[C:13](=[O:20])[N:12]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.[CH:38]1[CH:43]=[N:42][C:41]2[N:44](O)N=N[C:40]=2[CH:39]=1>C(Cl)Cl>[NH2:44][C:41]1[CH:40]=[C:39]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:17]([C:14]3[C:13](=[O:20])[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:11]([CH3:10])[C:15]=3[CH3:16])=[O:19])=[CH:3][C:4]=2[F:9])[CH:38]=[CH:43][N:42]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a suspension of 4-amino-2-fluorophenol (2.54 g, 20 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (4.74 g, 20.4 mmol) in DCM (60 mL) were added EDCI (4.6 g, 24 mmol) and HOAT (0.54 g, 4 mmol). The reaction was stirred at 45° C. for 12 hours, then cool to rt, quenched with H2O (10 mL), and stirred for another 4 hours. The solid was obtained by filtration and washed with DCM (20 mL×3), then dried at 60° C. in vacuo for 12 hours to give the title compound as a pale yellow solid (6.37 g, 93.4%).

Workup

temperaturecool to rt
customquenched with H2O (10 mL)
stirringstirred for another 4 hours
customThe solid was obtained by filtration
washwashed with DCM (20 mL×3)
customdried at 60° C. in vacuo for 12 hours

Sources & evidence

ORD record: ord-5f9fb3b78f59401593a75d28a6c74760
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969388B1

Reaction notes

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