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

HRID 1713568Notes

Reaction equation

HRID 1713568 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].[F:42][C:43]1[CH:44]=[C:45]([C:49]2([C:59]3[CH:64]=[CH:63][CH:62]=[C:61]([F:65])[CH:60]=3)[CH:53]3[CH2:54][NH:55][CH2:56][CH2:57][N:52]3[C:51](=[O:58])[O:50]2)[CH:46]=[CH:47][CH:48]=1>O1CCCC1.C(OCC)(=O)C>[F:42][C:43]1[CH:44]=[C:45]([C:49]2([C:59]3[CH:64]=[CH:63][CH:62]=[C:61]([F:65])[CH:60]=3)[CH:53]3[CH2:54][N:55]([C:30]([NH:1][CH2:2][CH2:3][N:4]([CH:17]4[CH2:19][CH2:18]4)[S:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[N+:14]([O-:16])=[O:15])(=[O:7])=[O:6])=[O:31])[CH2:56][CH2:57][N:52]3[C:51](=[O:58])[O:50]2)[CH:46]=[CH:47][CH:48]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 23121868N-(2-aminoethyl)-N-cyclopropyl-2-nitrobenzenesulfonamideHCID 231220271,1-Bis(3-fluorophenyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one

Product 1

HCID 231219611,1-Bis(3-fluorophenyl)-N-[2-[cyclopropyl[(2-nitrophenyl)sulfonyl]amino]ethyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamideYield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2-aminoethyl)-N-cyclopropyl-2-nitrobenzenesulfonamide (0.51 g, 1.8 mmol) and diisopropylethylamine (0.80 mL, 4.5 mmol) in tetrahydrofuran (20 mL) was added 4-nitrophenyl chloroformate (0.36 g, 1.8 mmol) with ice cooling, and the mixture was stirred at room temperature for 1 hour. 1,1-Bis(3-fluorophenyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.50 g, 1.5 mmol) was added thereto, and the mixture was stirred at room temperature overnight. To the reaction solution was added ethyl acetate, and the resulting mixture was sequentially washed with 1 N hydrochloric acid and a 1 N aqueous sodium hydroxide solution and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=49:1 to ethyl acetate), and then crystallized from ethyl acetate-diethyl ether to obtain the title compound (0.24 g, yield 25%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe resulting mixture was sequentially washed with 1 N hydrochloric acid
  3. dry with materiala 1 N aqueous sodium hydroxide solution and water, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=49:1 to ethyl acetate)
  6. customcrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-1eca35a81d304d94bfcd6ff2bf33a706
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

Loading…