HCID 67482917, compound → HCID 67482779, compound

HRID 1715514Notes

Reaction equation

HRID 1715514 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12](=O)[CH2:13][C:14]([O:16]CC)=O.FC(F)(F)C([O-])=O.[CH2:27]([O:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([C@@H:38]([NH2+:40][NH2:41])[CH3:39])=[CH:34][CH:33]=1)=[O:31])[CH3:28]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[C:12]1[CH2:13][C:14](=[O:16])[N:40]([C@H:38]([C:35]2[CH:36]=[CH:37][C:32]([C:30]([O:29][CH2:27][CH3:28])=[O:31])=[CH:33][CH:34]=2)[CH3:39])[N:41]=1

Participants

4

Reactant 2

HCID 67482917HCID 67482917, compoundHCID 86602022HCID 86602022, compound

Product 1

HCID 67482779HCID 67482779, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 3-[2-fluoro-5-(trifluoromethyl)phenyl]-3-oxopropanoate (3 g, 9.7 mmol) and {(1S)-1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinium trifluoroacetate (2.64 g, 8.2 mmol) were heated in dry acetonitrile (150 ml) to 85° C. for 8 hr. Solvent was evaporated and the residue purified by flash column chromatograph (SiO2, 25% ethyl acetate in hexanes) to give ethyl 4-((1S)-1-{3-[2-fluoro-5-(trifluoromethyl)phenyl]-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, 3H); 1.82 (d, 7.2 Hz, 3H); 3.81 (dd, J=3 Hz, 23.9 Hz, 1H); 3.87 (dd, J=3 Hz, 23.9 Hz, 1H); 4.36 (q, J=7.1 Hz, 2H); 5.60 (q, J=7.2 Hz, 1H); 7.25 (t, J=9.5 Hz, 1H); 7.51 (d, J=8.4 Hz, 2H): 7.66 (br, 1H); 8.03 (d, J=8.4 Hz, 2H); 8.25 (dd, J=1.8 Hz, 6.4 Hz, 1H). MS C21H18F4N2O3

Workup

  1. customSolvent was evaporated
  2. customthe residue purified by flash column chromatograph (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4f060831caaa4a0b99e99ba8aa967380
Source dataset
uspto-grants-2010_09
Patent number
US07799818B2

Reaction notes

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