Hydrazine → HCID 49806738, compound

HRID 576099Notes

Reaction equation

HRID 576099 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]4[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=4)=[CH:15][CH:16]=3)[CH:11]([CH3:25])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.NN>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]4[N:19]=[N:20][CH:21]=[CH:22][CH:23]=4)=[CH:15][CH:16]=3)[CH:11]([CH3:25])[NH:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 49806737HCID 49806737, compound

Product 1

HCID 49806738HCID 49806738, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product from Step F of Example 6, (190 mg, 0.51 mmol) in ethanol (15 mL) was added hydrazine (1 mL, 20.6 mmol) and 10% Pd/C (100 mg). The reaction mixture was heated at reflux for 1 hour. The mixture was then filtered through celite and the celite bed was washed with methanol. The filtrate was concentrated and purified by column chromatography (silica gel, 1% to 5% MeOH/CH2Cl2) to provide 4-(4-Chloro-phenyl)-7-(pyridazin-3-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline (99 mg, 57%): 1H NMR (CDCl3, 500 MHz) δ 9.15 (dd, J=4.9, 1.6 Hz, 1H), 8.05 (d, J=1.3 Hz, 1H), 7.83 (dd, J=8.6, 1.6 Hz, 1H), 7.69 (dd, J=8.1, 1.8 Hz, 1H), 7.53 (dd, J=8.6, 4.9 Hz, 1H), 7.29-7.26 (m, 2H), 7.08-7.05 (m, 2H), 6.98 (d, J=8.1 Hz, 1H), 4.35-4.33 (m, 1H), 4.19 (dd, J=7.9, 5.8 Hz, 1H), 3.49 (dd, J=12.8, 5.5 Hz, 1H), 3.02 (dd, J=12.8, 8.3 Hz, 1H), 1.59 (d, J=6.7 Hz, 3H). ESI MS m/z=336 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe mixture was then filtered through celite
  4. washthe celite bed was washed with methanol
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography (silica gel, 1% to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-af19e088fc6945579d7473bdcb14a703
Source dataset
uspto-grants-2015_05
Patent number
US09034899B2

Reaction notes

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