Ammonia → HCID 67981089, compound

HRID 1520029Notes

Reaction equation

HRID 1520029 reaction equation
N.[CH3:2][N:3]1[CH:8]2[CH2:9][CH2:10][CH:4]1[CH2:5][CH:6]([N:11]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[N:12]1)[CH2:7]2>CO.[Ni]>[CH3:2][N:3]1[CH:8]2[CH2:9][CH2:10][CH:4]1[CH2:5][CH:6]([N:11]1[CH:15]=[C:14]([NH2:16])[CH:13]=[N:12]1)[CH2:7]2

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86699010HCID 86699010, compound

Product 1

HCID 67981089HCID 67981089, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Ammonia was bubbled for 15 min in a solution of 8-Methyl-3-(4-nitro-1H-pyrazol-1-yl)-8-azabicyclo[3.2.1]octane (3.4 g, 14.4 mmol) in MeOH (300 mL). The solution was then hydrogenated (3 bars) in presence of Ra—Ni (2 g) at RT. After 2 h, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The solid was purified by trituration in acetonitrile (25 mL) to give the title compound as a white solid (2.2 g, 75%). 1H NMR (400 MHz, DMSO-d6) δ 7.08 (brs, 1H), 6.87 (brs, 1H), 4.49 (brs, 1H), 3.84 (s, 2H), 2.61 (s, 3H), 2.42-2.36 (m, 2H), 2.19-2.16 (t, 2H), 2.06-1.97 (m, 4H).

Workup

  1. customat RT
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe solid was purified by trituration in acetonitrile (25 mL)

Sources & evidence

ORD record
ord-c78d2353158843be8631cdd77d537c1d
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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