1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(5-hydroxypyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 872975Notes

Reaction equation

HRID 872975 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][N:10]1[C:14]([CH3:15])=[C:13]([C:16](O)=[O:17])[C:12](=[O:19])[N:11]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.O.CCOC(C)=O>[OH:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:16]([C:13]2[C:12](=[O:19])[N:11]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:10]([CH3:9])[C:14]=2[CH3:15])=[O:17])=[N:7][CH:6]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 42319722-Amino-5-hydroxypyridine

Product 1

HCID 90033479N-(5-hydroxypyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 6-aminopyridin-3-ol (330 mg, 3 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (710 mg, 306 mmol) in DMF (10 mL) was added EDCI (690 mg, 3.6 mmol) and HOAT (80 mg, 0.6 mmol). The reaction was stirred at 60° C. for 4 hours, then cooled to rt and diluted with water (100 mL) and EtOAc (2 mL). The mixture was cooled to 0° C. and stirred overnight. The resulted solid was collected through filtration to give title compound as a light brown solid (680 mg, 70%).

Workup

  1. temperaturecooled to rt
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringstirred overnight
  4. filtrationThe resulted solid was collected through filtration

Sources & evidence

ORD record
ord-8611df75bfa94361b4eab4d3d13edce8
Source dataset
uspto-grants-2015_03
Patent number
US08975282B2

Reaction notes

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