HCID 67355839, compound → HCID 67356043, compound

HRID 1850613Notes

Reaction equation

HRID 1850613 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=[O:25])[N:11]([C:16]1[CH:17]=[N:18][C:19]([N+:22]([O-])=O)=[CH:20][CH:21]=1)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[C:10](=[O:25])[N:11]([C:16]1[CH:17]=[N:18][C:19]([NH2:22])=[CH:20][CH:21]=1)[CH2:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67355839HCID 67355839, compound

Product 1

HCID 67356043HCID 67356043, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following nitro group reduction procedure 1, 3-(6-Nitro-pyridin-3-yl)-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (290 mg, 0.83 mmol) in methanol (10 mL) with nitrogen, then added 10% palladium on charcoal (200 mg, excess). Purged with hydrogen and allowed to stir under hydrogen atmosphere for 16 hours. Purged with nitrogen and filtered through a pad of celite, washing with methanol. Concentrated in vacuo which gave 3-(6-Amino-pyridin-3-yl)-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (146 mg, 60%). Used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.73 (d, J=2.6 Hz, 1H), 7.21 (dd, J=9.1, 2.6 Hz 1H), 6.43 (d, J=9.1 Hz, 1H), 6.01 (s, 2H), 4.38 (br. s, 1H), 4.26 (m, 1H), 3.77 (m, 1H), 3.30 (m, 1H), 2.17-2.07 (m, 2H), 2.02-1.95 (m, 2H), 1.43 (s, 9H); MS m/z 319.5 (MH+).

Workup

  1. customPurged with hydrogen
  2. customPurged with nitrogen
  3. filtrationfiltered through a pad of celite
  4. washwashing with methanol
  5. concentrationConcentrated in vacuo which

Sources & evidence

ORD record
ord-e26e3d68de81416e8e95989c3e4bb63a
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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