Benzene → HCID 67342213, compound

HRID 1670751Notes

Reaction equation

HRID 1670751 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]=[C:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:19]([CH2:22][CH3:23])CC)C.[CH:24]1C=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[NH:19][C:22](=[O:37])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=3[C:11]=2[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 130325691-Boc-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Product 1

HCID 67342213HCID 67342213, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid (synthesized according to the method described in Bioorg. Med. Chem., 8, 5, 2000, 1041-1058, 3.9 g), triethylamine (2.87 ml) and benzene (12 ml) was added diphenylphosphoryl azide (Aldrich Co., 4.44 ml) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was passed through a silica gel filter, and the filtrate was evaporated under reduced pressure to give a pale-yellow oil. Toluene (20 ml) was added to the oil, and the mixture was heated under reflux for 2 hr. The solvent was evaporated under reduced pressure. Dichloromethane (35 ml) and lead tetracetate (5.70 g) were added to the obtained residue. Thereafter, 1-aminobenzotriazole (Aldrich Co., 1.54 g) was dissolved in dichloromethane (15 ml) was added thereto. The mixture was stirred at room temperature for 30 min. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 6-oxo-1,4,5,6-tetrahydrobenzo[c]-1,7-naphthyridine-3(2H)-carboxylic acid tert-butyl ester (1.14 g, yield 33%).

Workup

  1. customsynthesized
  2. temperaturecooling
  3. filtrationfilter
  4. customthe filtrate was evaporated under reduced pressure
  5. customto give a pale-yellow oil
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 2 hr
  8. customThe solvent was evaporated under reduced pressure
  9. additionDichloromethane (35 ml) and lead tetracetate (5.70 g) were added to the obtained residue
  10. dissolutionThereafter, 1-aminobenzotriazole (Aldrich Co., 1.54 g) was dissolved in dichloromethane (15 ml)
  11. additionwas added
  12. stirringThe mixture was stirred at room temperature for 30 min
  13. filtrationThe reaction mixture was filtered
  14. customthe filtrate was evaporated under reduced pressure
  15. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6ce108ca5574082a649b9493e465ae8
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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