Diisopropylethylamine → HCID 23121899, compound

HRID 1713559Notes

Reaction equation

HRID 1713559 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.[C:33]1([C:39]2([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH:43]3[CH2:44][NH:45][CH2:46][CH2:47][N:42]3[C:41](=[O:48])[O:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1.O>[O:48]=[C:41]1[N:42]2[CH2:47][CH2:46][N:45]([C:22]([N:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[C:4](=[O:11])[CH2:3][CH2:2]3)=[O:24])[CH2:44][CH:43]2[C:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[O:40]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 1171582,3-dihydroquinolin-4(1H)-oneHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121899HCID 23121899, compoundYield 10.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydroquinolin-4(1H)-one (75 mg, 0.51 mmol) and diisopropylethylamine (0.25 mL) in tetrahydrofuran (3 mL) was added triphosgene (0.15 g, 0.51 mmol), and the mixture was stirred at room temperature for 20 minutes. Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.51 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 24 hours. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate), and then recrystallized from diisopropyl ether to obtain the title compound (25 mg, yield 10%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  8. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-0c48e9b818a24fc19c939000ec9380c7
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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