HCID 59226532, compound → tert-butyl 5-(3-aminopyridin-4-yl)-2-oxohexahydrobenzo[d]oxazole-3(2H)-carboxylate

HRID 73581Notes

Reaction equation

HRID 73581 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:11][CH2:12][CH:13]2[O:17][C:16](=[O:18])[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:14]2[CH:26]=1)([O-])=O>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:26][CH:14]2[N:15]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[C:16](=[O:18])[O:17][CH:13]2[CH2:12][CH2:11]1

Participants

5

Reactant 1

HCID 59226532HCID 59226532, compound

Product 1

HCID 59226567tert-butyl 5-(3-aminopyridin-4-yl)-2-oxohexahydrobenzo[d]oxazole-3(2H)-carboxylateYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate (1.0 equiv.) in methanol and ethyl acetate (1; 1, 0.1M) was added Pd/C (10%). The resulting mixture was stirred under H2 atmosphere for 6 hours. The solid was removed by filtration. The filtrate was concentrated under reduced pressure to give tert-butyl 5-(3-aminopyridin-4-yl)-2-oxohexahydrobenzo[d]oxazole-3(2H)-carboxylate (87%), which was used in the next step without further purification. LC/MS (m/z): MH+=334.1, Rt=0.51.

Workup

  1. customThe solid was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c14d7c7898584ccb80884431c1352535
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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