Hydrazine hydrate (1:1) → HCID 69311575, compound

HRID 860480Notes

Reaction equation

HRID 860480 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[C:14]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:15]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=2)[C:16]2[N:17]([C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=2)[N:18]=1.O.NN>C(O)C>[NH2:3][CH2:12][C:13]1[C:14]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:15]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=2)[C:16]2[N:17]([C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=2)[N:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69308730HCID 69308730, compound

Product 1

HCID 69311575HCID 69311575, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-7-ethyl-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazin-3-yl]pentanoate (107 mg) and hydrazine monohydrate (51.1 mg) in ethanol (2 mL) was heated under reflux for 2 hours. After evaporation of solvent, the residue was partitioned between chloroform and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give ethyl 5-[2-(aminomethyl)-7-ethyl-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazin-3-yl]pentanoate as yellow oil (67.6 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent
  4. customthe residue was partitioned between chloroform and saturated sodium bicarbonate solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-cdc3aa05c2f04e8caf8691a2136a625c
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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