Cyclohexene → HCID 86659259, compound

HRID 1803847Notes

Reaction equation

HRID 1803847 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]CC3C=CC=CC=3)=[CH:14][CH:15]=2)[C:10]([NH:25][C:26](=[O:53])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][C:28]=2[N:40]([CH:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[C:41](=[O:46])[C:42]([F:45])([F:44])[F:43])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCCCC=1>O1CCOCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([NH:25][C:26](=[O:53])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][C:28]=2[N:40]([CH:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[C:41](=[O:46])[C:42]([F:43])([F:44])[F:45])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 86659258HCID 86659258, compound

Product 1

HCID 86659259HCID 86659259, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-Benzyloxy-3-{4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzoylamino}-indazole-1-carboxylic acid tert-butyl ester (2.3 g, 3.13 mmol) in dioxane (46 mL) was treated with cyclohexene (18 mL) and 10% Pd/C (1.6 g). The mixture was stirred at reflux temperature. After 1.5 hs it was filtered over a celite funnel and washed with dioxane. Evaporation of the solvent left a solid that was washed with Et2O. After drying at 45° C. under vacuum, 1.92 g of title compound in 95% yield were obtained.

Workup

  1. temperatureat reflux temperature
  2. filtrationAfter 1.5 hs it was filtered over a celite funnel
  3. washwashed with dioxane
  4. customEvaporation of the solvent
  5. waitleft a solid
  6. washthat was washed with Et2O
  7. dry with materialAfter drying at 45° C. under vacuum, 1.92 g of title compound in 95% yield
  8. customwere obtained

Sources & evidence

ORD record
ord-d6643b0518634840b42335d78ed02c00
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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