HCID 67981147, compound → HCID 67981117, compound

HRID 1520030Notes

Reaction equation

HRID 1520030 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)[CH:8]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)[CH:8]=1

Participants

4

Reactant 1

HCID 67981147HCID 67981147, compound

Product 1

HCID 67981117HCID 67981117, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-Butyl 4-(4-nitro-1H-pyrazol-1-yl)azepane-1-carboxylate (4.5 g, 15.5 mmol) in methanol (250 mL) was hydrogenated (3 bars) in presence of Palladium on Carbon (10%, 2 g) at RT. After 3 h, the reaction mixture was filtered through a celite pad and concentrated under reduced pressure to give the title compound as a brown solid (3.8 g, 95%). 1H NMR: (400 MHz, DMSO-d6) δ 6.99 (s, 1H), 6.86 (s, 1H), 4.05 (m, 1H), 3.94 (m, 2H), 3.85 (m, 2H), 2.85 (brs, 2H), 1.86 (m, 2H), 1.65 (m, 2H), 1.40 (s, 9H).

Workup

  1. customat RT
  2. filtrationthe reaction mixture was filtered through a celite pad
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c12c53c1e0d4bc6978bfa708cfb8835
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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