Lithium hydroxide, monohydrate → 6-Cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:34])[NH:21][C:22]3[CH:23]=[N:24][C:25]4[C:30]([CH:31]=3)=[CH:29][CH:28]=[CH:27][C:26]=4[O:32][CH3:33])=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:35]([O:37]C)=[O:36])#[N:2].O[Li].O>C1COCC1.CO.C(O)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20](=[O:34])[NH:21][C:22]3[CH:23]=[N:24][C:25]4[C:30]([CH:31]=3)=[CH:29][CH:28]=[CH:27][C:26]=4[O:32][CH3:33])=[CH:18][CH:19]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:35]([OH:37])=[O:36])#[N:2]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of methyl 6-cyano-7-(4-(8-methoxyquinolin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.061 g, 0.120 mmol) in THF (2 mL) was added LiOH—H2O (0.239 mL, 0.239 mmol) and added a few drops of methanol to ensure a homogeneous solution. The reaction was stirred at ambient temperature for 3 hours. A few drops of acetic acid were added to the reaction and the solution concentrated to a yellow/white solid. The crude material was purified by silica gel column chromatography using 5% methanol/dichloromethane+0.1% acetic acid to provide the desired product (0.023 g, 39%). MS (APCI)=496.3 (M+1).
Workup
- concentrationthe solution concentrated to a yellow/white solid
- customThe crude material was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-a7b6436b49644e30b9e304e6026ad670
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785445B2
Reaction notes
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