Ethanol → HCID 86627655, compound

HRID 1907947Notes

Reaction equation

HRID 1907947 reaction equation
NN.O=[C:4]1[C:12]2C(=CC=CC=2)C(=O)[N:5]1[O:14][CH2:15][C:16]1[N:17]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:18]2[C:23]([CH3:24])=[C:22]([CH3:25])[N:21]3[N:26]=[N:27][N:28]=[C:20]3[C:19]=2[N:29]=1.[CH2:43](O)C>>[CH3:25][C:22]1[N:21]2[N:26]=[N:27][N:28]=[C:20]2[C:19]2[N:29]=[C:16]([CH2:15][O:14][N:5]=[C:4]([CH3:43])[CH3:12])[N:17]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:42])[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:18]=2[C:23]=1[CH3:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 67052377HCID 67052377, compound

Product 1

HCID 86627655HCID 86627655, compound

Procedure

Anhydrous hydrazine (0.47 mL, 15 mmol) was added to a stirred suspension of N-[4-(8-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butyl]benzamide (2.8 g, 5.0 mmol) in ethanol (50 mL). After two hours, a solid was isolated by filtration and the filter cake was washed with ethanol. Acetone (25 mL) and methanol (25 mL) were added to the solid and the mixture was stirred overnight. The volatiles were removed under reduced pressure to afford a solid that was triturated with 1 M aqueous sodium hydroxide (10 mL) and 1:1 methanol/acetone (4 mL). The solid was isolated by filtration, washed with water, and dissolved in chloroform (100 mL). The solution was dried over magnesium sulfate, filtered, concentrated under reduced pressure, and dried under vacuum to afford 1.9 g of a N-{4-[5,6-dimethyl-8-({[(1-methylethylidene)amino]oxy}methyl)-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}benzamide as a white solid.

Workup

  1. customa solid was isolated by filtration
  2. washthe filter cake was washed with ethanol
  3. additionAcetone (25 mL) and methanol (25 mL) were added to the solid
  4. customThe volatiles were removed under reduced pressure
  5. customto afford a solid
  6. customthat was triturated with 1 M aqueous sodium hydroxide (10 mL) and 1:1 methanol/acetone (4 mL)
  7. customThe solid was isolated by filtration
  8. washwashed with water
  9. dissolutiondissolved in chloroform (100 mL)
  10. dry with materialThe solution was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customdried under vacuum

Sources & evidence

ORD record
ord-e87fcd8044f646a08b9568ba510e51ca
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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