1,4-Cyclohexadiene → HCID 54576907, compound

HRID 1777714Notes

Reaction equation

HRID 1777714 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][CH:21]=[N:22]3)=[C:17]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CC=CCC=1>CCO.[OH-].[OH-].[Pd+2]>[N:25]1([C:17]2[N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][CH:11]=3)[CH:24]=[C:23]3[C:18]=2[CH:19]=[CH:20][CH:21]=[N:22]3)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 54576906HCID 54576906, compound

Product 1

HCID 54576907HCID 54576907, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of dibenzyl-[4-(5-morpholin-4-yl-[1,6]naphthyridin-7-yl)-phenyl]-amine B (30 mg, 0.06 mmol, leg) in dry EtOH (3 mL) was added Pd(OH)2 (16 mg, 50% w/w) and 1,4-cyclohexanediene (120 μL, 1.24 mmol, 20 eq) under Ar(g). The mixture was heated at 80° C. overnight; once cooled down, the reaction mixture was then filtered through a short celite pad, eluting with MeOH (10 mL). The solvent was subsequently removed in vacuo and the residue was further purified by silica gel column chromatography with hexane/EtOAc (1:4-0:1) to yield the product, C, as a pale yellow solid (9.6 mg, 51%).

Workup

  1. temperatureonce cooled down
  2. filtrationthe reaction mixture was then filtered through a short celite pad
  3. washeluting with MeOH (10 mL)
  4. customThe solvent was subsequently removed in vacuo
  5. customthe residue was further purified by silica gel column chromatography with hexane/EtOAc (1:4-0:1)
  6. customto yield the product, C

Sources & evidence

ORD record
ord-757b56c5545d4b11a3c939d70018f4f7
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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