Hydrochloric Acid → HCID 57940911, compound
Reaction equation
C(OCC[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][N:15]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:22]=2)[N:17]=[C:16]1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=1)(=O)C.[OH-:38].[Li+].O.Cl.O1CCCC1[CH2:47][CH2:48][OH:49]>>[CH3:37][O:36][C:32]1[CH:31]=[C:30]([C:16]2[N:15]([CH2:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:47][C:48]([OH:49])=[O:38])[C:23]3[C:18]([N:17]=2)=[N:19][CH:20]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=3)[CH:35]=[CH:34][CH:33]=1Participants
Procedure
[2-[[2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]methyl]phenoxy]ethyl acetate (Compound of Example 158) (28 mg) was dissolved in tetrahydrofuran-ethanol (1:1, v/v, 3.6 ml), and to the solution was added 2 N lithium hydroxide (1.2 ml). The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and to the mixture was added 2 N hydrochloric acid to adjust the pH to 3. The mixture was extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure and the resulting crystals were collected by filtration to obtain [2-[[2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]methyl]phenoxy]acetic acid (15 mg, 55%).
Workup
- extractionThe mixture was extracted with ethyl acetate-tetrahydrofuran (3:1
- washThe organic layer was washed with water
- dry with materialdried over MgSO4
- distillationThe solvent was distilled off under reduced pressure
- filtrationthe resulting crystals were collected by filtration
Sources & evidence
- ORD record
- ord-16dd71f82c2849f892f0af0a249e2c3e
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622479B2
Reaction notes
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