6-tert-Butylpyridin-2-amine → HCID 86699095, compound

HRID 1424205Notes

Reaction equation

HRID 1424205 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11](=O)[CH2:12]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](C(C)(C)C)[N:25]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]1[N:23]=[C:24]2[CH:29]=[CH:28][C:27]([C:2]([CH3:7])([CH3:3])[CH3:1])=[CH:26][N:25]2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 134946346-tert-Butylpyridin-2-amineHCID 86699120HCID 86699120, compound

Product 1

HCID 86699095HCID 86699095, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of tert-butyl {(1S)-1-[(benzyloxy)methyl]-3-bromo-2-oxopropyl}carbamate (3.72 g, 10.0 mmol) and 2-amino-6-tert-butylpyridine (1.5 g, 10.0 mmol) in toluene (50 mL) was stirred at room temperature for 14 hours and then refluxed for 5 hours. The reaction mixture was cooled and concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with 30% EtOAc in petroleum ether. The residue was treated with cold conc. HCl (5 mL) at 0° C. followed by stirring at room temperature for 18 hours. The reaction mixture was basified with saturated aqueous Na2CO3 solution, extracted with EtOAc, dried over Na2SO4 and concentrated in vacuo to afford a residue which was purified further by preparative TLC eluting with 20% MeOH in EtOAc to afford the title compound (21 mg, 25%).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by silica gel column chromatography
  5. washeluting with 30% EtOAc in petroleum ether
  6. additionThe residue was treated with cold conc. HCl (5 mL) at 0° C.
  7. stirringby stirring at room temperature for 18 hours
  8. extractionextracted with EtOAc
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto afford a residue which
  12. customwas purified further by preparative TLC
  13. washeluting with 20% MeOH in EtOAc

Sources & evidence

ORD record
ord-26ebc199a1ad496d9f1cddb68eb1c0a8
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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