Hydrazine hydrate (1:1) → HCID 69381849, compound

HRID 524349Notes

Reaction equation

HRID 524349 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[S:20]([CH3:23])(=[O:22])=[O:21])[CH2:5][N:6]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>CO.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[S:20]([CH3:23])(=[O:22])=[O:21])[CH2:5][NH2:6]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867116022-(3-Fluoro-4-methylsulfonyl-benzyl)-isoindole-1,3-dione

Product 1

HCID 69381849HCID 69381849, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

The purified intermediate 2-(3-fluoro-4-methylsulfonyl-benzyl)-isoindole-1,3-dione (5.50 g, 15.6 mmol) is dissolved in a mixture of methanol (250 mL) and dichloromethane (250 mL). Hydrazine hydrate (4.6 g, 78.4 mmol) is added, and the mixture is stirred at 60° C. for 3 h. The mixture is filtered, and the filtrate is treated with water. The mixture is extracted with ethyl acetate, and the organic layer is dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by preparative reversed-phase HPLC (Luna C18 250*50 mm, gradient of acetonitrile in water, 0.1% TFA). Yield: 3.1 g (81% of theory); ESI mass spectrum: [M+H]+=204; Retention time HPLC: 0.17 min (X012_S01).

Workup

  1. filtrationThe mixture is filtered
  2. additionthe filtrate is treated with water
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by preparative reversed-phase HPLC (Luna C18 250*50 mm, gradient of acetonitrile in water, 0.1% TFA)
  7. custom0.17 min (X012_S01)

Sources & evidence

ORD record
ord-b8e9dfaf4230490382e25d375f1dac02
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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