Methylhydrazine → HCID 28350836, compound

HRID 57398Notes

Reaction equation

HRID 57398 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([C@@H:13]([N:15]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:14])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CNN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([C@@H:13]([NH2:15])[CH3:14])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 90414565(S)-2-(1-(3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 28350836HCID 28350836, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (S)-2-(1-(3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethyl)isoindoline-1,3-dione (100 mg, 0.283 mmol) in ethanol (5 ml) was added methylhydrazine (16 μL, 0.311 mmol). Stir for 13 hours at 80° C. Concentrate in vacuo. Flash column chromatography (silica, 40 g) eluting with dichloromethane afforded 50 mg of desired product. HRMS m/z 224.4 (M+H)

Workup

  1. concentrationConcentrate in vacuo
  2. washFlash column chromatography (silica, 40 g) eluting with dichloromethane

Sources & evidence

ORD record
ord-c0484a65662f4d4782b8e2f99ba49d47
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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