Triethylamine → HCID 59764797, compound

HRID 406483Notes

Reaction equation

HRID 406483 reaction equation
[N:1]1([C:10](=[O:22])[C:11](N2C3C=CC=CC=3N=N2)=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Cl.[F:24][C:25]([F:37])([F:36])[C:26]1[CH:27]=[N:28][C:29]2[CH2:30][CH2:31][NH:32][CH2:33][C:34]=2[CH:35]=1.CCN(CC)CC>C1COCC1>[N:1]1([C:10](=[O:22])[C:11]([N:32]2[CH2:31][CH2:30][C:29]3[N:28]=[CH:27][C:26]([C:25]([F:36])([F:24])[F:37])=[CH:35][C:34]=3[CH2:33]2)=[O:12])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3549039HCID 3549039, compoundHCID 601460143-(Trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine--hydrogen chloride (1/1)

Product 1

HCID 59764797HCID 59764797, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,2-bis-benzotriazol-1-yl-ethane-1,2-dione (0.100 g, 0.342 mmol) in THF (3.4 mL) was added 3-trifluoromethyl-5,6,7,8-tetrahydro-[1,6]naphthyridine monohydrochloride (0.082 g, 0.342 mmol) and the reaction mixture was stirred at ambient temperature for about 4 h. Et3N (0.05 mL, 0.34 mmol) was added and stirring was resumed for about 1 hour. The reaction mixture was concentrated in vacuo and the residue triturated from hot iPrOAc. The solid was removed by filtration and the filtrate concentrated in vacuo then dissolved in EtOAc (10 mL), washed with 1N aq NaOH (2×5 mL), and saturated aqueous NaHCO3 (10 mL). The organic portion was separated, dried over MgSO4, filtered, and concentrated in vacuo to provide 1-benzotriazol-1-yl-2-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-ethane-1,2-dione as an orange oil (0.056 g, 0.15 mmol). The crude material was used without further purification.

Workup

  1. stirringstirring
  2. waitwas resumed for about 1 hour
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue triturated from hot iPrOAc
  5. customThe solid was removed by filtration
  6. concentrationthe filtrate concentrated in vacuo
  7. dissolutionthen dissolved in EtOAc (10 mL)
  8. washwashed with 1N aq NaOH (2×5 mL), and saturated aqueous NaHCO3 (10 mL)
  9. customThe organic portion was separated
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4680ac9d5eed4f21a13eb74c08fe21f5
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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