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

HRID 520705Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[N:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=O)[O:26]C4C=CC=CC=4)[CH:19]=3)=[CH:13][CH:12]=2)=[O:9])[C:4](=[O:34])[N:3]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[NH2:41][CH2:42][CH2:43][OH:44]>CN1C(=O)CCC1>[OH:44][CH2:43][CH2:42][NH:41][C:25](=[O:26])[NH:24][C:20]1[CH:19]=[C:18]([O:17][C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:34])[N:3]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[N:16][CH:15]=2)[CH:23]=[CH:22][N:21]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of phenyl (4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate (0.1 g, 0.187 mmol), NMP (10 mL) and 2-aminoethanol (14.0 mg, 0.224 mmol) was heated at 40° C. for 2 hours. The solvent was evaporated under reduced pressure at 40° C., and then diluted with EtOAc (20 mL). The precipitate was collected by filtration and washed with EtOAc (3 mL) to give the title compound as a white solid (92 mg, 98%).

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-aee2775cb95e4860b5a2714bb236ebe0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326975B2

Reaction notes

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