Water → Diisopropyl 5-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H, 3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene) amino]phenyl}dihydro-2,4,6-trioxo-s-triazine-1,3 (2H,4H)-diacetate

HRID 1488Notes

Reaction equation

HRID 1488 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]=[C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][N:13]3[C:12](=[O:19])[S:11]2)=[CH:4][C:3]=1[N:20]1[C:25](=[O:26])[NH:24][C:23](=[O:27])[N:22]([CH2:28][C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[C:21]1=[O:35].C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][C:44]([O:46][CH:47]([CH3:49])[CH3:48])=[O:45].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]=[C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][N:13]3[C:12](=[O:19])[S:11]2)=[CH:4][C:3]=1[N:20]1[C:25](=[O:26])[N:24]([CH2:43][C:44]([O:46][CH:47]([CH3:49])[CH3:48])=[O:45])[C:23](=[O:27])[N:22]([CH2:28][C:29]([O:31][CH:32]([CH3:33])[CH3:34])=[O:30])[C:21]1=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 19690745isopropyl 3-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]-pyridazin-1-ylidene)amino]phenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 86752188Diisopropyl 5-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H, 3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene) amino]phenyl}dihydro-2,4,6-trioxo-s-triazine-1,3 (2H,4H)-diacetateYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of isopropyl 3-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]-pyridazin-1-ylidene)amino]phenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.85 g, 1.62 mmol), potassium carbonate (0.27 g, 1.95 mmol) and isopropyl bromoacetate (0,353 g, 1.95 mmol)in N,N-dimethylformamide is stirred overnight at room temperature and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extract is washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an orange gel. Flash column chromatography of the gel using silica gel and an ethyl acetate/hexanes solution (2:3) gives the title product as a yellow gel (0.3 g) which is identified by NMR spectral analysis.

Workup

  1. extractionThe aqueous mixture is extracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an orange gel

Sources & evidence

ORD record
ord-7a8f9c1c64f84e7eae13346d27dfc137
Source dataset
uspto-grants-1998_03
Patent number
US05726126

Reaction notes

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