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

HRID 520728Notes

Reaction equation

HRID 520728 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].CCN(CC)CC.[CH3:12][N:13]1[C:17]([CH3:18])=[C:16]([C:19]([NH:21][C:22]2[CH:44]=[CH:43][C:25]([O:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33][C:34](=O)[O:35]C4C=CC=CC=4)[CH:28]=3)=[CH:24][CH:23]=2)=[O:20])[C:15](=[O:45])[N:14]1[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN1C(=O)CCC1>[CH2:2]([NH:4][C:34](=[O:35])[NH:33][C:29]1[CH:28]=[C:27]([O:26][C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:19]([C:16]3[C:15](=[O:45])[N:14]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:13]([CH3:12])[C:17]=3[CH3:18])=[O:20])=[CH:44][CH:43]=2)[CH:32]=[CH:31][N:30]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 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 73051696N-(4-((2-(3-ethylureido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 50.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of ethylamine hydrochloride (29 mg, 0.356 mmol) was in NMP (3 mL) was added Et3N (0.1 mL). The solution was stirred at rt for 10 minutes, followed by the addition 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). The reaction was stirred at 40° C. overnight, then concentrated in vacuo at 40° C., and 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)=80/40/1) to give the title compound as a white solid (46 mg, 50%).

Workup

  1. stirringThe reaction was stirred at 40° C. overnight
  2. concentrationconcentrated in vacuo at 40° C.
  3. additiondiluted with water (10 mL)
  4. filtrationThe precipitate was collected by filtration
  5. custompurified by a silica gel column chromatography (DCM/EtOAc/MeOH (v/v/v)=80/40/1)

Sources & evidence

ORD record
ord-fbd5fcfe00c643d6be2eb76822a7d7ef
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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