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

HRID 873019Notes

Reaction equation

HRID 873019 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)=[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][NH:42][CH2:43][CH2:44][OH:45]>CN1C(=O)CCC1>[OH:45][CH2:44][CH2:43][N:42]([CH3:41])[C:23](=[O:31])[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:34])[N:3]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:9])=[CH:12][CH:13]=2)[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 131732558phenyl(4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)pyridin-2-yl)carbamate

Product 1

HCID 73051862N-(4-((2-(3-(2-hydroxyethyl)-3-methylureido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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 (50 mg, 0.093 mmol), NMP (3 mL) and 2-(methylamino)ethanol (8.4 mg, 0.112 mmol) was heated at 40° C. for 2 hours. The solvent was evaporated under reduced pressure at 40° C., and then diluted with EtOAc (10 mL). The resulted mixture was washed with water (7 mL×3), followed by washing with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was washed with EtOAc (2 mL) to give the title compound as a white solid (25 mg, 52%).

Workup

  1. customThe solvent was evaporated under reduced pressure at 40° C.
  2. additiondiluted with EtOAc (10 mL)
  3. washThe resulted mixture was washed with water (7 mL×3)
  4. washby washing with brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washThe residue was washed with EtOAc (2 mL)

Sources & evidence

ORD record
ord-24af8d8506374711ae44944572e115a8
Source dataset
uspto-grants-2015_03
Patent number
US08975282B2

Reaction notes

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