4-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-2-nitro-phenylamine → 4-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-benzene-1,2-diamine

HRID 970016Notes

Reaction equation

HRID 970016 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([N+:23]([O-])=O)[CH:17]=3)=[CH:12][CH:11]=1)[CH2:2]2>CCO.[Pd]>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[N:14][C:13]([C:16]3[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=3)=[CH:12][CH:11]=1)[CH2:2]2

Participants

4

Reactant 1

HCID 114165594-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-2-nitro-phenylamine

Product 1

HCID 113813724-{6-[(3R)-1-Aza-bicyclo[2.2.2]oct-3-yloxy]-pyridazin-3-yl}-benzene-1,2-diamineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of Example 34D (200 mg, 0.59 mmol) was hydrogenated under the catalysis of Pd/C (Aldrich, 10 wt. %, 50 mg) in EtOH (10 mL) under hydrogen at ambient temperature for 10 h. After the reaction went to completion, the catalyst was removed through a short column of diatomaceous earth (˜2 g) and the filtrate was washed with EtOH (2×5 mL). The ethanol solution was concentrated to give the title compound (180 mg, yield, 98%). 1H NMR (500 MHz, CD3-OD) δ 1.58-1.73 (m, 1 H), 1.76-2.00 (m, 2 H), 2.06-2.27 (m, 1 H), 2.29-2.47 (m, 1 H), 2.81-3.20 (m, 5 H), 3.52-3.68 (m, 1 H), 5.11-5.57 (m, 1 H), 6.78 (d, J=8.2 Hz, 1 H), 7.12-7.26 (m, 2H), 7.32 (d, J=2.1 Hz, 1 H), 7.92 (d, J=9.2 Hz, 1 H) ppm. MS (DCl/NH3): 312 (M+H)+.

Workup

  1. customthe catalyst was removed through a short column of diatomaceous earth (˜2 g)
  2. washthe filtrate was washed with EtOH (2×5 mL)
  3. concentrationThe ethanol solution was concentrated

Sources & evidence

ORD record
ord-c5a13be0b91b4b3f9ea686b5768d1ea5
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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