Ethanol → HCID 86726649, compound

HRID 1499392Notes

Reaction equation

HRID 1499392 reaction equation
CCO.[N+:4]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1[N:17]1[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:18]1)=[CH:14][CH:13]=[CH:12][CH:11]=2)([O-])=O.[NH4+].[Cl-]>[Fe].O>[NH2:4][C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1[N:17]1[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:18]1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 86726648HCID 86726648, compound

Product 1

HCID 86726649HCID 86726649, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

EtOH (5.00 mL) followed by water (1.00 mL) were added to a vial containing tert-butyl [(3S)-1-(3-nitroquinolin-4-yl)piperidin-3-yl]carbamate (118.9 mg, 0.3193 mmol), iron powder (199.0 mg, 3.563 mmol) and NH4Cl (288.9 mg, 5.401 mmol). The mixture was stirred at 80° C. for 1 h. The reaction mixture was filtered through a pad of diatomaceous earth. The pad was eluted with a 10% aq. K3PO4 (20 mL), and EtOAc (20 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a pale yellow solid (36.9 mg, 34%). LCMS calc. for C19H27N4O2 (M+H)+: m/z=343.2. found 343.2.

Workup

  1. additionwere added to
  2. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  3. washThe pad was eluted with a 10% aq. K3PO4 (20 mL), and EtOAc (20 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e303d68e1c194bd893388ce51b51258a
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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