HCID 21913932, compound → HCID 21913266, compound

HRID 1245981Notes

Reaction equation

HRID 1245981 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]1[C:22]2[C:21]([CH3:23])=[C:20]([CH3:24])[N:19]3[N:25]=[N:26][N:27]=[C:18]3[C:17]=2[N:16]=[C:15]1[CH2:28][CH3:29])(=[O:7])=[O:6]>CN(C=O)C>[O:6]=[S:5]1(=[O:7])[CH2:4][CH2:3][CH2:2][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]1[C:22]2[C:21]([CH3:23])=[C:20]([CH3:24])[N:19]3[N:25]=[N:26][N:27]=[C:18]3[C:17]=2[N:16]=[C:15]1[CH2:28][CH3:29]

Participants

3

Reactant 1

HCID 21913932HCID 21913932, compound

Product 1

HCID 21913266HCID 21913266, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 1,8-diazabicyclo[5.4.0]undecene-7 (4.2 mL, 28 mmol) was added to a solution of 3-chloro-N-{2-[2-(8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)ethoxy]ethyl}propane-1-sulfonamide (2.50 g, 5.63 mmol) in DMF (50 mL), and the reaction was stirred overnight at room temperature. The solution was concentrated to about 25 mL under reduced pressure, and water (300 mL) was added. A white precipitate formed, which was isolated by filtration and recrystallized from acetonitrile (20 mL) to provide 1.95 g of 7-{2-[2-(1,1-dioxidoisothiazolidin-2-yl)ethoxy]ethyl}-8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine as white crystals, m. p. 176–178° C.

Workup

  1. concentrationThe solution was concentrated to about 25 mL under reduced pressure, and water (300 mL)
  2. additionwas added
  3. customA white precipitate formed
  4. customwhich was isolated by filtration
  5. customrecrystallized from acetonitrile (20 mL)

Sources & evidence

ORD record
ord-dc0aaf515c1346dcaa597143b8bbade1
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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