Sodium Hydroxide → HCID 59000805, compound

HRID 1594020Notes

Reaction equation

HRID 1594020 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:30]([O:32]CC)=[O:31])=[C:8]([CH2:27][CH2:28][CH3:29])[N:9]2[C:14]=1[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:30]([OH:32])=[O:31])=[C:8]([CH2:27][CH2:28][CH3:29])[N:9]2[C:14]=1[C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:10]2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11662701HCID 11662701, compound

Product 1

HCID 59000805HCID 59000805, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-morpholin-4-yl-4-phenyl-7-propyl-pyrrolo[1,2-b]pyridazine-5,6-dicarboxylic acid diethyl ester (15) (3.9 g, 8.38 mmol) and 10 mL of a 2N solution of NaOH in 50 mL of ethanol and 30 mL of water was heated at reflux for 5 h. The reaction mixture was cooled to r.t. and concentrated to about half of the original volume. 25 mL of 1N HCl were added and the resulting precipitate was collected by vacuum filtration, washed with cold water and died in vacuo to provide the title compound as a solid. 1H NMR (DMSO-d6) δ 1.04-1.10 (m, 6H), 1.79-1.87 (m, 2H), 3.34 (t, 2H, 7.3 Hz), 3.66-3.74 (m, 6H), 3.86-3.91 (m, 4H), 6.91 (s, 1H), 7.56-7.64 (m, 5H), 12.53 (brs, 1H). Mass Spectrum (ES+) m/e=460.1 (M+23).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. concentrationconcentrated to about half of the original volume
  4. addition25 mL of 1N HCl were added
  5. filtrationthe resulting precipitate was collected by vacuum filtration
  6. washwashed with cold water

Sources & evidence

ORD record
ord-a4e2fd8b07b84dc0bced3e6c580caeaa
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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