Diisopropylamine → HCID 23122071, compound

HRID 1713565Notes

Reaction equation

HRID 1713565 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:35])[O:31][CH2:32][CH2:33]Br.C(NC(C)C)(C)C.[NH:44]1[CH2:49][CH:48]=[CH:47][CH2:46][CH2:45]1>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[N:44]1([CH2:33][CH2:32][O:31][C:30]([N:13]2[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]3[CH2:12]2)=[O:35])[CH2:45][CH:46]=[CH:47][CH2:48][CH2:49]1

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 127501,2,3,6-TetrahydropyridineHCID 785282-Bromoethyl chloroformateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122071HCID 23122071, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.50 mmol) was dissolved in tetrahydrofuran (5 mL). Triethylamine (0.14 mL, 1.0 mmol) and 2-bromoethyl chlorocarbonate (0.10 g, 0.55 mmol) were added thereto, and the mixture was stirred at room temperature for 1 hour. Diisopropylamine (0.36 mL, 2.0 mmol), N,N-dimethylformamide (5 mL) and 1,2,3,6-tetrahydropyridine (0.23 mL, 2.5 mmol) were sequentially added thereto, and the mixture was stirred at room temperature for 24 hours. To the reaction solution was added ethyl acetate, and 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 amino silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate), and then crystallized from diisopropyl ether to obtain the title compound (0.13 g, yield 59%).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate)
  6. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-084f48b18414445493704f3b7ccbe2ac
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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