HCID 71230561, compound → HCID 71230590, compound

HRID 1746276Notes

Reaction equation

HRID 1746276 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11]C(=O)OCC2C=CC=CC=2)[C:5](=[O:22])[NH:4][NH:3]1>CO.[Pd]>[NH2:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:2](=[O:1])[NH:3][NH:4][C:5]1=[O:22]

Participants

4

Reactant 1

HCID 71230561HCID 71230561, compound

Product 1

HCID 71230590HCID 71230590, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To benzyl 4-(3,5-dioxo-1,2,4-triazolidin-4-yl)butylcarbamate (I-9b: 369 mg, 1.205 mmol) in methanol (4.819 mL) was added 10% Pd/C (51.3 mg, 0.048 mmol). The mixture was stirred at room temperature for 1 hour under 1 atm of H2, filtered over celite, rinsed with more methanol, concentrated in vacuo and dried to give 4-(4-aminobutyl)-1,2,4-triazolidine-3,5-dione (I-9c: 105 mg, 51%) as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 1.51-1.79 (m, 4 H) 2.94 (t, J=7.20 Hz, 2 H) 3.50 (t, J=6.57 Hz, 2 H).

Workup

  1. filtrationfiltered over celite
  2. washrinsed with more methanol
  3. concentrationconcentrated in vacuo
  4. customdried

Sources & evidence

ORD record
ord-46ae4cb87d5d449ea7b337bd95ba12c2
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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