Diisopropylethylamine → N-[2-[Cyclopropyl[(2-nitrophenyl)sulfonyl]amino]ethyl]-tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide

HRID 1713563Notes

Reaction equation

HRID 1713563 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH:17]1[CH2:19][CH2:18]1)[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6].C(N(C(C)C)CC)(C)C.Cl[C:30](OC1C=CC([N+]([O-])=O)=CC=1)=[O:31].[C:42]1([C:48]2([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH:52]3[CH2:53][NH:54][CH2:55][CH2:56][N:51]3[C:50](=[O:57])[O:49]2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1.C(OCC)(=O)C>[CH:17]1([N:4]([S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])[CH2:3][CH2:2][NH:1][C:30]([N:54]2[CH2:55][CH2:56][N:51]3[C:50](=[O:57])[O:49][C:48]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=4)[CH:52]3[CH2:53]2)=[O:31])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 23121868N-(2-aminoethyl)-N-cyclopropyl-2-nitrobenzenesulfonamideHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23122026N-[2-[Cyclopropyl[(2-nitrophenyl)sulfonyl]amino]ethyl]-tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamideYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2-aminoethyl)-N-cyclopropyl-2-nitrobenzenesulfonamide (0.47 g, 1.7 mmol) and diisopropylethylamine (0.71 mL, 4.1 mmol) in tetrahydrofuran (15 mL) was added 4-nitrophenyl chloroformate (0.33 g, 1.7 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hour. Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.40 g, 1.4 mmol) was added thereto, and the mixture was stirred at room temperature for 60 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with 1 N hydrochloric acid, a 1 N aqueous sodium hydroxide solution, water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=98:2 to ethyl acetate). The fractions were collected and concentrated. The residue was washed with diethyl ether and collected by filtration to obtain the title compound (0.76 g, yield 92%).

Workup

  1. stirringthe mixture was stirred at room temperature for 60 hours
  2. washthe resulting mixture was washed with 1 N hydrochloric acid
  3. dry with materiala 1 N aqueous sodium hydroxide solution, water and saturated brine, and dried over magnesium sulfate
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=98:2 to ethyl acetate)
  7. customThe fractions were collected
  8. concentrationconcentrated
  9. washThe residue was washed with diethyl ether
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-34eb4416e33f4285a5ce6642af5dbbe6
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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