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

HRID 870449Notes

Reaction equation

HRID 870449 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[CH3:11][N:12]1[C:16]([CH3:17])=[C:15]([C:18](O)=[O:19])[C:14](=[O:21])[N:13]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O>[Cl:8][C:7]1[CH:6]=[C:5]([OH:9])[C:4]([F:10])=[CH:3][C:2]=1[NH:1][C:18]([C:15]1[C:14](=[O:21])[N:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:12]([CH3:11])[C:16]=1[CH3:17])=[O:19]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 112406564-Amino-5-chloro-2-fluorophenol

Product 1

HCID 90033637N-(2-chloro-5-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 53.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-amino-5-chloro-2-fluorophenol (0.97 g, 6 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (1.42 g, 6.12 mmol) in DMF (20 mL) was added EDCI (0.38 mg, 7.2 mmol) and HOAT (0.16 g, 1.2 mmol). The mixture was allowed to warm up to 80° C. and stirred for 24 hours. Then H2O (200 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at 0° C. for 2 hours, then filtered to give the title compound as a light brown solid (1.2 g, 53.2%).

Workup

  1. stirringThe resulted mixture was stirred at 0° C. for 2 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-082c2cfe38cd4ebba04c371abd807db4
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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