Ethanol → HCID 67585642, compound

HRID 617352Notes

Reaction equation

HRID 617352 reaction equation
C(O)(=O)/C=C/C(O)=O.[CH3:9][N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[CH2:15][O:16][C:17]1[N:18]=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=1.C(O)C.C(N(CC)CC)C>C(OCC)(=O)C.[Pd]>[ClH:23].[ClH:23].[CH3:9][N:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[CH2:15][O:16][C:17]1[N:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 88299650HCID 88299650, compound

Product 1

HCID 67585642HCID 67585642, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 92.8 mg (0.27 mmol) sample of 3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)-6-chloropyridazine fumarate, from Example 12 above, was dissolved in 10 mL of a 4:1 mixture of ethyl acetate:ethanol, and 0.124 mL (0.89 mmol) of triethylamine and 5 mg of 10% Pd/C were added. The mixture was hydrogenated under 1 atm of H2 for 30 minutes, then the catalyst was removed by filtration. The solvents were removed under vacuum, to the residue was added 20 mL of satd NaHCO3 solution, and the mixture was extracted with methylene chloride. The solution was dried over MgSO4 and taken to dryness, the residue was azeotroped with ethanol several times to remove residual triethylamine. The residue was treated with HCl in ether according to Example 14c to afford 40 mg of the title compound. mp 176-177° C. MS (DCI/NH3) m/e: 194 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.89 (dd, 1H, J=4.6, 1.3 Hz), 7.75 (dd, 1H, J=9.0, 4.6 Hz), 7.38 (dd, 1H, J=9.0, 1.3 Hz), 4.84 (dd, 1H, J=12.3, 3.1 Hz), 4.67 (dd, 1H, J=12.3, 6.1 Hz), 3.98 (m, 1H), 3.76 (m, 1H), 3.26 (m, 1H), 3.04 (s, 3H), 2.41 (m, 1H), 2.23 (m, 1H). Anal. Calc. for C10H17Cl2N3O.0.3 HCl: C, 43.34; H, 6.29; N, 15.11; Found C, 43.23; H, 6.19; N, 14.78.

Workup

  1. customthe catalyst was removed by filtration
  2. customThe solvents were removed under vacuum, to the residue
  3. additionwas added 20 mL of satd NaHCO3 solution
  4. extractionthe mixture was extracted with methylene chloride
  5. dry with materialThe solution was dried over MgSO4
  6. customthe residue was azeotroped with ethanol several times
  7. customto remove residual triethylamine
  8. additionThe residue was treated with HCl in ether according to Example 14c

Sources & evidence

ORD record
ord-0b03027a6ce64866b20fca435d5ec275
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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