Hydrazine hydrate (1:1) → HCID 86727391, compound

HRID 519029Notes

Reaction equation

HRID 519029 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([O:13][C:14]2[C:15]([F:32])=[CH:16][C:17]3[O:22][CH2:21][C:20](=S)[N:19]([CH:24]([C:26](OCC)=[O:27])[CH3:25])[C:18]=3[CH:31]=2)([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:34][NH2:35]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([O:13][C:14]2[CH:31]=[C:18]3[C:17](=[CH:16][C:15]=2[F:32])[O:22][CH2:21][C:20]2[N:19]3[CH:24]([CH3:25])[C:26](=[O:27])[NH:34][N:35]=2)([CH3:12])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86727390HCID 86727390, compound

Product 1

HCID 86727391HCID 86727391, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[4-(1-ethoxycarbonyl-ethyl)-7-fluoro-3-thioxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.080 g, 0.171 mmol) in EtOH (5 mL) was added hydrazine hydrate (0.085 g, 1.707 mmol) and the mixture was heated to reflux for 2 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether) to give 3-(7-fluoro-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.033 g, 46%) as a white solid. LC/MS (Table 1, Method 2) Rt=1.144 min.; MS m/z: 421 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto 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-223be83c87f740759e6483538c22cf73
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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