{2-[4-[1,3]Dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester → 3-(4-Fluoro-phenyl)-2-isopropyl-7,8-dihydro-2H-1,2,6-triaza-azulene-6-carboxylic acid benzyl ester

HRID 606624Notes

Reaction equation

HRID 606624 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH2:12][C:13]1[C:17]([CH2:18][CH:19]2OCCO2)=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:15]([CH:31]([CH3:33])[CH3:32])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.O>[CH2:1]([O:8][C:9]([N:10]1[CH2:11][CH2:12][C:13]2[C:17](=[C:16]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:15]([CH:31]([CH3:32])[CH3:33])[N:14]=2)[CH:18]=[CH:19]1)=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 54754013{2-[4-[1,3]Dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester

Product 1

HCID 177536273-(4-Fluoro-phenyl)-2-isopropyl-7,8-dihydro-2H-1,2,6-triaza-azulene-6-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {2-[4-[1,3]dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester (0.5 g, 1.1 mmol) in TFA (10 mL) and water (2 mL) was heated at reflux for 2 h. The mixture was concentrated and the residue was purified by FCC to provide the title compound. HPLC: RT=11.00 min. MS (ESI): mass calcd. for C24H24FN3O2, 405.19; m/z found, 406.3 [M+H]+.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-c1286b9f475a426f98d52534ba228182
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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