Dichloromethane → HCID 86627654, compound

HRID 599417Notes

Reaction equation

HRID 599417 reaction equation
NN.[CH:3]1([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:24]([CH3:26])=[C:23]([CH3:27])[N:22]4[N:28]=[N:29][N:30]=[C:21]4[C:20]=3[N:19]=[C:18]2[CH2:31][O:32][N:33]2C(=O)C3[C:35](=CC=CC=3)[C:34]2=O)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[CH2:45]Cl>C(O)C>[CH:3]1([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C:25]3[C:24]([CH3:26])=[C:23]([CH3:27])[N:22]4[N:28]=[N:29][N:30]=[C:21]4[C:20]=3[N:19]=[C:18]2[CH2:31][O:32][N:33]=[C:34]([CH3:45])[CH3:35])=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 67052220HCID 67052220, compound

Product 1

HCID 86627654HCID 86627654, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Anhydrous hydrazine (0.50 mL, 16.1 mmol) was added to a stirred suspension of N-cyclohexyl-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]urea (3.00 g, 5.36 mmol) in ethanol (36 mL). Over the next hour, dichloromethane (40 mL) and ethanol (20 mL) were added to prevent the reaction from solidifying. After one more hour, the solvent was removed under reduced pressure, then acetone (27 mL) and methanol (27 mL) were added. The mixture was stirred at room temperature for 2 hours, then a solid was isolated by filtration and washed with methanol. To the solid was added 1 M aqueous sodium hydroxide and the mixture was sonicated for 1 minute. The solid was isolated by filtration, washed with water, and dried under vacuum at 70° C. to provide 2.36 g of N-cyclohexyl-N′-{4-[5,6-dimethyl-8-({[(1-methylethylidene)amino]oxy}methyl)-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}urea.

Workup

  1. customthe reaction from solidifying
  2. customAfter one more hour, the solvent was removed under reduced pressure
  3. additionacetone (27 mL) and methanol (27 mL) were added
  4. customa solid was isolated by filtration
  5. washwashed with methanol
  6. additionTo the solid was added 1 M aqueous sodium hydroxide
  7. customthe mixture was sonicated for 1 minute
  8. customThe solid was isolated by filtration
  9. washwashed with water
  10. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-4ce4865587ab42ba80dc2397eb6aaf35
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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