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

HRID 873012Notes

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)=[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.[CH3:42][NH:43][CH2:44][CH3:45]>CN1C(=O)CCC1>[CH2:44]([N:43]([CH3:42])[C:23](=[O:24])[NH:22][C:18]1[CH:17]=[C:16]([O:15][C:14]2[CH:32]=[CH:33][C:11]([NH:10][C:8]([C:5]3[C:4](=[O:35])[N:3]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[CH:12][C:13]=2[F:34])[CH:21]=[CH:20][N:19]=1)[CH3:45]

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 N-methylethanamine (12 mg, 0.2 mmol) was heated at 40° C. for 2 hours. 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/MeOH (v/v)=60/1) to give the title compound as a white solid (55 mg, 62%).

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/MeOH (v/v)=60/1)

Sources & evidence

ORD record: ord-24345f5e2ee141be977e5dac2c7a0541
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975282B2

Reaction notes

Loading…