Triethylamine → HCID 58501887, compound

HRID 2097677Notes

Reaction equation

HRID 2097677 reaction equation
[NH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.CN(C1C=CC=CN=1)C.[O:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]1[N:53]=[N:54][NH:55][C:56]=1[C:57]([O:59][CH2:60][CH3:61])=[O:58])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O>[N:1]1([C:19]([N:55]2[C:56]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[C:52]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=3[O:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:53]=[N:54]2)=[O:21])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 92911DecahydroquinolineHCID 94429TriphosgeneHCID 178470429HCID 178470429, compound

Product 1

HCID 58501887HCID 58501887, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of decahydroquinoline (10) (1.5 equiv) in dry dichloromethane (0.5 M) under argon was added triethylamine (1.5 equiv) followed by triphosgene (1.5 equiv). The resulting heterogeneous mixture was stirred at room temperature for 15 minutes, concentrated in vacuo. The residue was taken up in dry toluene (0.25 M with respect to amine), treated with dimethylaminopyridine (DMAP) (1.0 equiv) and triazole (9) (1.0 equiv). The resulting mixture was heated to reflux for 1.5 hours, cooled to room temperature and diluted with ethyl acetate and brine, and the aqueous and organic layers were separated. The organic layer was washed with brine, 10% aqueous HCl, then brine, and dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes) to provide ethyl 1-(decahydroquinoline-1-carbonyl)-4-(2-phenoxyphenyl)-1H-1,2,3-triazole-5-carboxylate (11) as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 1.5 hours
  4. temperaturecooled to room temperature
  5. customthe aqueous and organic layers were separated
  6. washThe organic layer was washed with brine, 10% aqueous HCl
  7. dry with materialbrine, and dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5ab02473171841cba6c8d6809dd5b177
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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