Hydrazine hydrate (1:1) → (4,5,6,7-Tetrahydro-1H-indazol-5-yl)-carbamic acid tert-butyl ester

HRID 1425407Notes

Reaction equation

HRID 1425407 reaction equation
O.[NH2:2]N.C[N:5]([CH:7]=[C:8]1[C:13](=O)[CH2:12][CH2:11][CH:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)C>CO>[NH:2]1[C:13]2[CH2:12][CH2:11][CH:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9][C:8]=2[CH:7]=[N:5]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67317686HCID 67317686, compound

Product 1

HCID 67316380(4,5,6,7-Tetrahydro-1H-indazol-5-yl)-carbamic acid tert-butyl esterYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine monohydrate (0.11 mL, 2.35 mmol) was added to a solution of tert-butyl {3-[(dimethylamino)methylene]-4-oxocyclohexyl}carbamate obtained in Example (242a) (526 mg, 1.96 mmol) in methanol (10 mL), and the mixture was heated under reflux for 18 hours. The reaction solution was concentrated. The resulting residue was azeotropically distilled with toluene and then purified by silica gel column chromatography (elution solvent: dichloromethane/methanol 20/1) to obtain 257 mg of the title compound as an amorphous compound (55%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction solution was concentrated
  4. distillationThe resulting residue was azeotropically distilled with toluene
  5. custompurified by silica gel column chromatography (elution solvent: dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-51a474c8e5c4438c852d0871ff93661a
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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