Acetic Acid → 6-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid
Reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[OH-].[Na+].C(O)(=O)C.CCOC(C)=O>C1COCC1>[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Methyl 6-amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinate (0.550 g, 1.47 mmol) was dissolved in THF (15 mL) and then treated with 1.0 M NaOH (7.33 mL, 7.33 mmol). The reaction mixture was heated to 50° C. Once the reaction was done by TLC, the reaction was cooled to room temperature and then acidified with acetic acid. The reaction mixture was taken up in of EtOAc (˜15 mL) then extracted with H2O (2×15 mL). The water layer then was re-washed with EtOAc (˜15 mL) and the combined organic layers were dried over anhydrous Na2SO4(s). The mixture was then filtered and concentrated in vacuo to give the title compound (0.495 g, 1.37 mmol).
Workup
- temperaturethe reaction was cooled to room temperature
- extractionthen extracted with H2O (2×15 mL)
- washThe water layer then was re-washed with EtOAc (˜15 mL)
- dry with materialthe combined organic layers were dried over anhydrous Na2SO4(s)
- filtrationThe mixture was then filtered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bcc4d7442ec440879fda0e22466ba556
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383825B2
Reaction notes
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