HCID 67421578, compound → HCID 67420337, compound

HRID 1987363Notes

Reaction equation

HRID 1987363 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-])=O)=[N:4][CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[CH3:20][C:19]1[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][CH:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]2[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH2:28])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 67421578HCID 67421578, compound

Product 1

HCID 67420337HCID 67420337, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3,3″-dimethyl-1′-(2-nitro-benzyl)-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.55 g, 1.37 mmol) in MeOH (20 mL) was added palladium (50% wet with water), 10 wt.% on activated carbon (0.113 g). The resultant mixture was hydrogenated at 30 psi on a Parr shaker for 3 hours. The mixture was vacuum filtered through celite and the cake was washed with MeOH. The solvent was removed from the filtrate under reduced pressure and the thus obtained oil was purified by radial chromatography on silica gel (2 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH) and provided 80 mg (16%) of COMPOUND 65 as a white solid. 1H NMR (CDCl3) δ 1.49-1.72 (m, 3H), 1.88-1.95 (m, 1H), 2.06-2.20 (m, 2H), 2.36 (s, 6H), 3.33 (s, 2H), 3.75 (dd, 2H, J=11.7, 3.0 Hz), 4.47 (br s, 2H), 6.07 (dd, 2H, J=7.5, 6.0 Hz), 6.42-6.45 (m, 1H), 6.54 (td, 1H, J=7.5, 1.2 Hz), 6.87 (dd, 2H, J=7.5, 4.8 Hz), 7.15 (d, 2H, J=7.5 Hz), 8.33 (d, 2H, J=3.9 Hz); ES-MS m/z 373 (M+H).

Workup

  1. filtrationfiltered through celite
  2. washthe cake was washed with MeOH
  3. customThe solvent was removed from the filtrate under reduced pressure
  4. customthe thus obtained oil was purified by radial chromatography on silica gel (2 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-ae074d8d6a53439ab779e2fe5ad42af0
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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