Triethylamine → HCID 23121852, compound

HRID 1713547Notes

Reaction equation

HRID 1713547 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2C(O)=O)[CH:4]=[CH:3][CH:2]=1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]1([C:44]2([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH:48]3[CH2:49][NH:50][CH2:51][CH2:52][N:47]3[C:46](=[O:53])[O:45]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[O:53]=[C:46]1[N:47]2[CH2:52][CH2:51][N:50]([C:19]([NH:16][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[N:1]=[CH:2][CH:3]=[CH:4]4)=[O:28])[CH2:49][CH:48]2[C:44]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[O:45]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 665828-Quinolinecarboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121852HCID 23121852, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Quinolinecarboxylic acid (0.17 g, 1.0 mmol) was suspended in toluene (5 mL). With ice cooling, triethylamine (0.14 mL, 1.0 mmol) and diphenylphosphoryl azide (0.28 g, 1.0 mmol) were sequentially added thereto, and the mixture was stirred at room temperature for 1 hour and then at 80° C. for 3 hour. After cooling to 50° C., tetrahydrofuran (5 mL) and hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (88 mg, 0.30 mmol) were added thereto, and the mixture was stirred at 50° C. overnight. The reaction solution was cooled to room temperature and ethyl acetate was added thereto. The resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate) to obtain the title compound (46 mg, yield 33%).

Workup

  1. waitat 80° C. for 3 hour
  2. temperatureAfter cooling to 50° C.
  3. stirringthe mixture was stirred at 50° C. overnight
  4. temperatureThe reaction solution was cooled to room temperature
  5. washThe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate)

Sources & evidence

ORD record
ord-44d0e06fee8643cd816a7af73bf93e1f
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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