Hydrochloric Acid → 5-[3-Butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-benzoic acid
Reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:37])[C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([O:18][CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[N:15]=[N:14][C:13]=2[CH2:26][CH2:27][CH2:28][CH3:29])[CH:9]=[CH:8][C:7]=1[O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.Cl>C1COCC1.CO>[CH2:26]([C:13]1[N:14]=[N:15][C:16]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[CH:17][C:12]=1[C:10]1[CH:9]=[CH:8][C:7]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:6]([CH:11]=1)[C:5]([OH:37])=[O:4])[CH2:27][CH2:28][CH3:29]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
2 N aq. lithium hydroxide solution (2.5 mmol, 1.25 mL) was added to a solution of 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-benzoic acid methyl ester (Example 71, 0.615 mmol, 296 mg) in THF (5 mL) and MeOH (1.25 mL). It was stirred overnight. Aq. HCl solution was added to adjust pH to neutral. The reaction mixture was partitioned between DCM (20 mL) and water (20 mL). The DCM layer was separated and dried over sodium sulfate. The organic solvents were removed in vacuo to give 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-benzoic acid.
Workup
- customThe reaction mixture was partitioned between DCM (20 mL) and water (20 mL)
- customThe DCM layer was separated
- dry with materialdried over sodium sulfate
- customThe organic solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-bfdde5b898b44f799ecd261acc24f2d8
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045461B2
Reaction notes
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