HCID 68427937, compound → HCID 60170607, compound

HRID 1715509Notes

Reaction equation

HRID 1715509 reaction equation
C(OC(=O)CC(C1C=C(Cl)C=C(Cl)C=1)=O)C.[Cl:17][C:18]1[CH:19]=[C:20]([C:25]2[CH2:29][C:28](=[O:30])[N:27]([C@H:31]([C:33]3[CH:43]=[CH:42][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:35][CH:34]=3)[CH3:32])[N:26]=2)[CH:21]=[C:22]([Cl:24])[CH:23]=1.FC(F)(F)C([O-])=O.C(OC(C1C=CC([C@@H]([NH2+]N)C)=CC=1)=O)C>C(#N)C>[Cl:17][C:18]1[CH:19]=[C:20]([C:25]2[CH2:29][C:28](=[O:30])[N:27]([C@H:31]([C:33]3[CH:43]=[CH:42][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:35][CH:34]=3)[CH3:32])[N:26]=2)[CH:21]=[C:22]([Cl:24])[CH:23]=1

Participants

4

Reactant 2

HCID 68427937HCID 68427937, compoundHCID 86602022HCID 86602022, compound

Product 1

HCID 60170607HCID 60170607, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Step A Ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]ethyl}benzoate Ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate (4.2 g, 16.1 mmol) and {(1S)-1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinium trifluoroacetate (5.2 g, 16.1 mmol) were heated in dry acetonitrile (100 ml) to 85° C. for 1 hr. The solvent was removed under reduced pressure, and the residue purified by column chromatography (SiO2, 20% ethyl acetate in hexanes) to give ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]ethyl}benzoate as a white solid. NMR (500 MHz, CDCl3) δ: 1.38 (t, J=7.1 Hz, 3H); 1.78 (d, J=7.0 Hz, 3H); 3.55 (d, J=22.6 Hz, 1H); 3.60 (d, J=22.6 Hz, 1H); 4.36 (q, J=7.1 Hz, 2H); 5.57 (q, J=7.0 Hz, 1H); 7.39 (t, J=1.9 Hz, 1H); 7.50 (d, J=8.4 Hz, 2H). 7.52 (d, J=1.9 Hz, 2H); 8.02 (d, J=8.4 Hz, 2H). MS C20H18Cl2N2O3 Cald: 404.07; Obsd (M+1): 405.20.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography (SiO2, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-eb3cddd0e2464d0292978c25857825b4
Source dataset
uspto-grants-2010_09
Patent number
US07799818B2

Reaction notes

Loading…