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

HRID 520706Notes

Reaction equation

HRID 520706 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:33])OC4C=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.[CH3:41][N:42]1C(=O)C[CH2:44][CH2:43]1.CNCCO.[OH2:53]>CCOC(C)=O>[OH:53][CH2:44][CH2:43][N:42]([CH3:41])[C:25](=[O:33])[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

6

Reactant 4

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 13387N-methyl-2-pyrrolidoneHCID 131732556phenyl (4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate

Product 1

HCID 73052019N-(5-((2-(3-(2-hydroxyethyl)-3-methylureido)pyridin-4-yl)oxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 (30 mg, 0.05 mmol), NMP (5 mL) and 2-(methylamino)ethanol (5.0 mg, 0.06 mmol) was heated at 40° C. for 1.5 hours. The mixture was cooled to rt, and diluted with EtOAc (15 mL) and water (10 mL). The separated organic layer was washed with water (10 mL×3), followed by washing with brine (10 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=20/1), and then washed with ether (5 mL) to give the title compound as a white solid (17 mg, 59%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. washThe separated organic layer was washed with water (10 mL×3)
  3. washby washing with brine (10 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=20/1)
  7. washwashed with ether (5 mL)

Sources & evidence

ORD record
ord-36bd7b82eacc49789da20908f627330d
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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