Ethanolamine → N-(3-fluoro-4-((2-(3-(2-hydroxyethyl)ureido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 520716Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23](=[O:31])OC4C=CC=CC=4)[CH:17]=3)=[C:13]([F:34])[CH:12]=2)=[O:9])[C:4](=[O:35])[N:3]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[NH2:42][CH2:43][CH2:44][OH:45]>CN1C(=O)CCC1>[F:34][C:13]1[CH:12]=[C:11]([NH:10][C:8]([C:5]2[C:4](=[O:35])[N:3]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:2]([CH3:1])[C:6]=2[CH3:7])=[O:9])[CH:33]=[CH:32][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]([NH:42][CH2:43][CH2:44][OH:45])=[O:31])[CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of phenyl (4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)pyridin-2-yl)carbamate (100 mg, 0.18 mmol), NMP (5 mL) and 2-aminoethanol (3.0 mg, 0.22 mmol) was heated at 40° C. for 2 hours. The solvent was evaporated under reduced pressure at 40° C., and diluted with EtOAc (20 mL). The precipitate was collected by filtration, and then washed with EtOAc (3 mL) to give the title compound as a white solid (65 mg, 69%).

Workup

customThe solvent was evaporated under reduced pressure at 40° C.
additiondiluted with EtOAc (20 mL)
filtrationThe precipitate was collected by filtration
washwashed with EtOAc (3 mL)

Sources & evidence

ORD record: ord-2523657177004f85b9149728f5dc3b52
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326975B2

Reaction notes

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