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

HRID 520717Notes

Reaction equation

HRID 520717 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][CH:44]([OH:46])[CH3:45].[CH3:47]N1C(=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]([N:42]([CH2:43][CH:44]([OH:46])[CH3:45])[CH3:47])=[O:31])[CH:17]=1

Participants

4

Reactant 3

HCID 41-Amino-2-propanolHCID 13387N-methyl-2-pyrrolidoneHCID 131732557phenyl(4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)pyridin-2-yl)carbamate

Product 1

HCID 73052184N-(3-fluoro-4-((2-(3-(2-hydroxypropyl)-3-methylureido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 60%

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 1-aminopropan-2-ol (16 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 EtOAc (20 mL). The precipate was collected by filtration to give the title compound as a white solid (58 mg, 60%).

Workup

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

Sources & evidence

ORD record
ord-5e09b4b4b2114fb8a323e4593e07e414
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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