Chlorosuccinimide → Tert-butyl (z)-((6-(chloro(hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)carbamate

HRID 40394Notes

Reaction equation

HRID 40394 reaction equation
[OH:1]/[N:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][N:12]=2)[N:9]=1.[Cl:22]N1C(=O)CCC1=O>CN(C=O)C>[Cl:22]/[C:3](=[N:2]\[OH:1])/[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[N:11][N:12]=2)[N:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 135987477tert-butyl N-[[6-[(E)-hydroxyiminomethyl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]carbamate

Product 1

HCID 135987468Tert-butyl (z)-((6-(chloro(hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved (E)-tert-butyl (6-((hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (200 mg, 0.684 mmol) in 25 mL of DMF and added 1-chloropyrrolidine-2,5-dione (95.9 mg, 0.718 mmol). Let stir at rt for 2 h. Poured reaction mixture onto water (20 mL) and extracted with ether (3×20 mL). Washed organics with water (2×20 mL), brine (1×20 ml), dried over sodium sulfate, filtered and concentrated. Title compound used without further purification (220 mg, 97% yield).

Workup

  1. additionPoured
  2. customreaction mixture onto water (20 mL)
  3. extractionextracted with ether (3×20 mL)
  4. dry with materialWashed organics with water (2×20 mL), brine (1×20 ml), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customTitle compound used without further purification (220 mg, 97% yield)

Sources & evidence

ORD record
ord-eb0251f2793b4ef6ad5ae5dcdedaa13f
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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