1-methyl-4-(5-nitro-2-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-1,4-dihydro-5H-tetrazol-5-one → 1-(5-amino-2-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-one

HRID 633407Notes

Reaction equation

HRID 633407 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[N:17]2[CH2:22][CH2:21][N:20]([CH:23]3[CH2:26][O:25][CH2:24]3)[CH2:19][CH2:18]2)[N:4]=[N:3]1>CCO.CO.[Pd]>[NH2:14][C:12]1[CH:11]=[CH:10][C:9]([N:17]2[CH2:22][CH2:21][N:20]([CH:23]3[CH2:26][O:25][CH2:24]3)[CH2:19][CH2:18]2)=[C:8]([N:5]2[C:6](=[O:7])[N:2]([CH3:1])[N:3]=[N:4]2)[CH:13]=1

Participants

4

Reactant 1

HCID 867045031-methyl-4-(5-nitro-2-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-1,4-dihydro-5H-tetrazol-5-one

Product 1

HCID 867045041-(5-amino-2-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-4-methyl-1,4-dihydro-5H-tetrazol-5-oneYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

1-methyl-4-(5-nitro-2-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)-1,4-dihydro-5H-tetrazol-5-one (0.75 g, 1.0 eq, 2.1 mmol) was suspended in a mixture of EtOH/MeOH (1:1, 100 mL) in a 250 mL round bottom flask and the reaction flask was charged with Pd—C (10% loading, 0.25 g). The reaction flask was evacuated under house vacuum and subsequently filled with hydrogen while stirring. This procedure was repeated three times and the reaction mixture was stirred for 3 hours under an H2 balloon. The mixture was filtered through celite and the filter cake was washed with MeOH (2×10 mL). The filtrate was concentrated on a rotovap to leave a white solid which upon high vacuum drying gave the product in 78% yield.

Workup

  1. customThe reaction flask was evacuated under house vacuum
  2. additionsubsequently filled with hydrogen
  3. stirringthe reaction mixture was stirred for 3 hours under an H2 balloon
  4. filtrationThe mixture was filtered through celite
  5. washthe filter cake was washed with MeOH (2×10 mL)
  6. concentrationThe filtrate was concentrated on a rotovap
  7. customto leave a white solid which upon high vacuum
  8. customdrying
  9. customgave the product in 78% yield

Sources & evidence

ORD record
ord-c93ba53e7292434a9575a52cf3767d30
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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