Dichloromethane → HCID 86711623, compound

HRID 527353Notes

Reaction equation

HRID 527353 reaction equation
NN.[F:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[S:22]([CH3:27])(=[N:24][C:25]#[N:26])=[O:23])[CH2:7][N:8]1C(=O)C2C(=CC=CC=2)C1=O.ClCCl>CO>[F:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[S:22]([CH3:27])(=[N:24][C:25]#[N:26])=[O:23])[CH2:7][NH2:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9321HydrazineHCID 86711622HCID 86711622, compound

Product 1

HCID 86711623HCID 86711623, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine (85% in water, 2.0 g, 53 mmol) is added to a solution of 2-(3-fluoro-4-(N-cyano-S-methylsulfonimidoyl)-benzyl)-isoindole-1,3-dione (preparation 15c, 3.5 g, 8.8 mmol) in a 1:1 mixture of dichloromethane and methanol (140 mL). The mixture is stirred over night and concentrated under reduced pressure. The residue is purified by preparative reversed phase HPLC (Luna C18(2), gradient of acetonitrile in water, 0.01 M NH3). Yield: 1.2 g (58% of theory); ESI mass spectrum: [M+H]+=228; r.t. HPLC: 0.26 min (X011_S03).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by preparative reversed phase HPLC (Luna C18(2), gradient of acetonitrile in water, 0.01 M NH3)
  3. customr.t
  4. custom0.26 min (X011_S03)

Sources & evidence

ORD record
ord-d4d841b3d4dd4508a0d9c37101a450dc
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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