3-(4-Fluoro-phenyl)-2-isopropyl-7,8-dihydro-2H-1,2,6-triaza-azulene-6-carboxylic acid benzyl ester → 3-(4-Fluoro-phenyl)-2-isopropyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

HRID 606627Notes

Reaction equation

HRID 606627 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:14](=[C:15]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=2)[CH:13]=[CH:12]1)=O)C1C=CC=CC=1>C(O)(C)C.[Pd]>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:15]2[N:16]([CH:21]([CH3:23])[CH3:22])[N:17]=[C:18]3[C:14]=2[CH2:13][CH2:12][NH:11][CH2:20][CH2:19]3)=[CH:25][CH:26]=1

Participants

4

Reactant 1

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

Product 1

HCID 113916543-(4-Fluoro-phenyl)-2-isopropyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 3-(4-fluoro-phenyl)-2-isopropyl-7,8-dihydro-2H-1,2,6-triaza-azulene-6-carboxylic acid benzyl ester (0.2 g, 0.49 mmol) and 10% Pd/C (20 mg) in isopropanol (20 mL) was subjected to H2 (45 psi) at rt for 16 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by FCC to give the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-e3edcb07a16d4b7ab0edb46b21f181e1
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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