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

HRID 520727Notes

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)[O:24]C4C=CC=CC=4)[CH:17]=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.[CH3:41][NH2:42]>CN1C(=O)CCC1>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]([NH:42][CH3:41])=[O:24])[CH:17]=3)=[CH:32][CH:33]=2)=[O:9])[C:4](=[O:34])[N:3]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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)phenoxy)pyridin-2-yl)carbamate (100 mg, 0.187 mmol), NMP (3 mL) and methylamine solution (25%, 0.2 mL) was heated at 40° C. overnight. The solvent was evaporated under reduced pressure at 40° C., and then diluted with water (10 mL). The precipitate was collected by filtration, and then purified by a silica gel column chromatography (DCM/EtOAc/MeOH (v/v/v)=1/1/0.01) to give the title compound as a white solid (46 mg, 52%).

Workup

customThe solvent was evaporated under reduced pressure at 40° C.
additiondiluted with water (10 mL)
filtrationThe precipitate was collected by filtration
custompurified by a silica gel column chromatography (DCM/EtOAc/MeOH (v/v/v)=1/1/0.01)

Sources & evidence

ORD record: ord-b9aa024ce6c7439290ab5607e1756427
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326975B2

Reaction notes

Loading…