Tert-butyl 4-aminophenethylcarbamate → HCID 21876379, compound

HRID 858476Notes

Reaction equation

HRID 858476 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:12])[N:3]=1.[C:13]([O:17][C:18](=[O:29])[NH:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)([CH3:16])([CH3:15])[CH3:14]>C(N(CC)C(C)C)(C)C>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:28][C:25]2[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][NH:19][C:18](=[O:29])[O:17][C:13]([CH3:15])([CH3:14])[CH3:16])=[CH:27][CH:26]=2)[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 2

HCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 21876379HCID 21876379, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of 2,4-dichloro-6-methyl-3-nitro-pyridine (Chorvat, Robert J. et al., J. Med. Chem., 1999, 42, 833., 7.5 g, 36.2 mmol), [2-(4-amino-phenyl)-ethyl]-carbamic acid tert-butyl ester (Stark, Peter A. et al., J. Med. Chem., 1992, 35, 4264., 1.14 g, 4.83 mmol) in N,N-diisopropylethylamine (50 ml) was heated at reflux temperature for 16 h. After cooling, the mixture was concentrated. The residue was diluted with dichloromethane (200 ml) and washed with saturated aqueous NaHCO3 solution (50 ml×2). The organic layer was dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with hexane/ethyl acetate (1:1) to afford 310 mg (16%) of the title compound as orange solids.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated
  5. additionThe residue was diluted with dichloromethane (200 ml)
  6. washwashed with saturated aqueous NaHCO3 solution (50 ml×2)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by flash column chromatography
  10. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1ea2eea511494c8e9f88cc0c7e0343d1
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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