Hydrazine → HCID 86627657, compound

HRID 599422Notes

Reaction equation

HRID 599422 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>C(O)C>[CH:4](=[N:5][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)[CH3:12]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67052377HCID 67052377, compound

Product 1

HCID 86627657HCID 86627657, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous hydrazine (0.481 mL, 15.3 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 (prepared as described in Part B of Example 89, 2.86 g, 5.11 mmol) in ethanol (50 mL). The reaction was stirred overnight and then was concentrated under reduced pressure. Methanol (25 mL) was added and the mixture was cooled to 0° C. Acetaldehyde (2.9 mL) was added and the reaction mixture was stirred overnight. The reaction mixture was concentrated partially under reduced pressure, then 1 M aqueous sodium hydroxide (50 mL) was added 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 a 3:1 ratio of oxime isomers of N-{4-[8-({[ethylideneamino]oxy}methyl)-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl]butyl}benzamide.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionMethanol (25 mL) was added
  3. additionAcetaldehyde (2.9 mL) was added
  4. stirringthe reaction mixture was stirred overnight
  5. concentrationThe reaction mixture was concentrated partially under reduced pressure
  6. addition1 M aqueous sodium hydroxide (50 mL) was added
  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-476bc4d1c5ff4883acdff45263716ab0
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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