Ethyl Acetate → HCID 71238524, compound

HRID 1846629Notes

Reaction equation

HRID 1846629 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][C:18]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>[Pd].CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:20]([NH2:21])=[CH:19][C:18]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:17][N:16]=2)[CH2:13][CH2:14]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 71238714HCID 71238714, compound

Product 1

HCID 71238524HCID 71238524, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.03 g (2.48 mmol) of (5′-methanesulfonyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylmethyl)-carbamic acid tert-butyl ester and 0.15 g (0.14 mmol) of 10% palladium on carbon in a 1:1 mixture of ethyl acetate:methanol (50 mL) is placed under an atmosphere of hydrogen and stirred overnight at room temperature. The mixture is filtered through diatomaceous earth and the filter pad is washed with methanol. The filtrate is concentrated under reduced pressure to provide 0.980 g (103%) of as a (3′-amino-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylmethyl)-carbamic acid tert-butyl ester as a brown resin.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. washthe filter pad is washed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb6b20c11a9f41e1b8ad34ff15a4c7e3
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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