HCID 56777233, compound → HCID 58380653, compound

HRID 1715124Notes

Reaction equation

HRID 1715124 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH2:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 56777233HCID 56777233, compound

Product 1

HCID 58380653HCID 58380653, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(3-nitro-pyridin-4-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (25.0 g, 77.55 mmol, 1.0 equiv) in ethanol (375 mL) was added palladium on activated charcoal 10% (2.5 g, 2.35 mmol, 0.03 equiv) and the reaction put under hydrogen (50 Psi) in a Parr shaker for 16 h. The reaction mixture was filtered through Celite and the filtrate evaporated under reduced pressure. The residue was triturated with diethyl ether, the organic layer decanted and the solid material dried under reduced pressure to yield 18.4 g (81%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.25-1.27 (m, 2H), 1.40 (s, 9H), 1.88-1.91 (m, 2H), 2.90 (br s, 2H), 3.49 (br s, 1H), 3.89 (br s, 2H), 4.57 (s, 2H), 5.05 (br s, 1H), 6.42 (d, J=4.3 Hz, 1H), 7.56 (d, J=4.3 Hz, 1H), 7.63 (s, 1H). MS (ISP): 293.4 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was triturated with diethyl ether
  4. customthe organic layer decanted
  5. customthe solid material dried under reduced pressure

Sources & evidence

ORD record
ord-08fb702c1cf540b7b0f5978761348776
Source dataset
uspto-grants-2010_09
Patent number
US07799806B2

Reaction notes

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