Hydrazine → tert-Butyl 8-methyl-5,8-dihydropyrido[3,4-c]pyridazine-7(6H)-carboxylate

HRID 132872Notes

Reaction equation

HRID 132872 reaction equation
O[CH:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH3:18])[C:6]1=O)[CH:3]=O.[NH2:20][NH2:21]>C1C=CC=CC=1>[CH3:18][CH:7]1[C:6]2[N:20]=[N:21][CH:3]=[CH:2][C:5]=2[CH2:10][CH2:9][N:8]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86604215tert-Butyl 4-(1-hydroxyl-2-oxoethyl)-2-methyl-3-oxopiperidine-1-carboxylate

Product 1

HCID 69192961tert-Butyl 8-methyl-5,8-dihydropyrido[3,4-c]pyridazine-7(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 70.0 mg (0.258 mmol) of tert-butyl 4-(1-hydroxyl-2-oxoethyl)-2-methyl-3-oxopiperidine-1-carboxylate (Step E) in 12 mL of benzene was added hydrazine. The reaction was heated to reflux for 3.5 h and concentrated to afford the title compound. LC/MS 194 (M+1-56).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3.5 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-50b9e332bcbb408281a97cb0bd3503cb
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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