Hydrazine hydrate (1:1) → HCID 86727359, compound

HRID 519003Notes

Reaction equation

HRID 519003 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][C:20](=S)[N:19]([CH:24]([C:26]([O:28]CC)=O)[CH3:25])[C:18]=3[CH:31]=2)([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:33][NH2:34]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([CH3:12])([O:13][C:14]2[CH:31]=[C:18]3[C:17](=[CH:16][CH:15]=2)[O:22][CH2:21][C:20]2[N:19]3[CH:24]([CH3:25])[C:26](=[O:28])[NH:33][N:34]=2)[CH2:11]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727358HCID 86727358, compound

Product 1

HCID 86727359HCID 86727359, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[4-(1-ethoxycarbonyl-ethyl)-3-thioxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.095 g, 0.211 mmol) in EtOH (5 mL) was added hydrazine hydrate (0.105 g, 2.109 mmol) and the mixture was heated at reflux for 2 h. The reaction mixture was cooled to ambient temperature, concentrated in vacuo and the residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether) to give 3-methyl-3-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (0.064 g, 75%) as a white solid. LC/MS (Table 1, Method 2) Rt=1.143 min.; MS m/z: 403 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-0c213bc5eb8141b89cc41cee78438094
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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