1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)picolinamide

HRID 520678

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[C:23]([CH3:24])=[C:22]([C:25](O)=[O:26])[C:21](=[O:28])[N:20]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.O>[CH3:18][N:19]1[C:23]([CH3:24])=[C:22]([C:25]([NH:1][C:2]2[N:7]=[CH:6][C:5]([O:8][C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH2:17])=[O:16])[CH:10]=3)=[CH:4][CH:3]=2)=[O:26])[C:21](=[O:28])[N:20]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a suspension of 4-((6-aminopyridin-3-yl)oxy)picolinamide (230 mg, 1 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (237 mg, 1.02 mmol) in DCM (5 mL) was added EDCI (230 mg, 1.2 mmol) and HOAT (27 mg, 0.2 mmol). The reaction was stirred at 45° C. for 28 hours, then cooled to rt and diluted with water (10 mL) and DCM (20 mL). The organic phase was concentrated in vacuo and the residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=40/1) to give the title compound as a light grey solid (111 mg, 25%).

Workup

temperaturecooled to rt
concentrationThe organic phase was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=40/1)

Sources & evidence

ORD record: ord-1619e4cb056440a19f65efca89f1c326
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326975B2

Linked notes

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