Chloroacetyl chloride → HCID 23122070, compound

HRID 1713537Notes

Reaction equation

HRID 1713537 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(C(C)C)CC)(C)C.Cl[CH2:33][C:34](Cl)=[O:35].[F:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1>O1CCCC1.O>[F:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][CH2:33][C:34]([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])=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 97314-FluoroanilineHCID 81531DiisopropylethylamineHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122070HCID 23122070, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.20 g, 0.68 mmol) was dissolved in tetrahydrofuran (3 mL). With ice cooling, diisopropylethylamine (1 mL) and chloroacetyl chloride (70 μL, 0.82 mmol) were added thereto, and the mixture was stirred at room temperature for 3 hours. Next, 4-fluoroaniline (0.13 mL, 1.4 mmol) was added thereto, and the mixture was stirred at 50° C. for 16 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from hexane to obtain the title compound (45 mg, yield 15%).

Workup

  1. stirringthe mixture was stirred at 50° C. for 16 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  6. customcrystallized from hexane

Sources & evidence

ORD record
ord-31f8582238fc4926a04bbdeaaaa9b184
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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