Reaction equation
Cl.[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.[C:18]1([CH:24]2[CH2:28][CH2:27][CH2:26][NH:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C>[O:17]=[C:15]([N:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[CH:14]=[CH:13]/[C:8]1[CH:7]=[C:6]2[C:11](=[N:10][CH:9]=1)[NH:12][C:3](=[O:2])[CH2:4][CH2:5]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (30 mg, 0.12 mmol), DMF (3 mL), 2-phenylpyrrolidine (21 mg, 0.14 mmol), DIPEA (48 μL, 0.28 mmol) and EDAC (27 mg, 0.14 mmol). The reaction mixture was stirred at room temperature and concentrated to dryness. LC/MS showed the presence of the target compound and no starting material after 24 h. The residue was purified on preparative TLC (eluent: dichloromethane/NH3 7N in MeOH, 2.5%) to give a pale yellow solid. This solid as triturated in acetone, filtered, washed with acetone and dried to give the title compound (7 mg, 17%) as a white solid.
Workup
- concentrationconcentrated to dryness
- customThe residue was purified on preparative TLC (eluent: dichloromethane/NH3 7N in MeOH, 2.5%)
- customto give a pale yellow solid
- customThis solid as triturated in acetone
- filtrationfiltered
- washwashed with acetone
- customdried
Sources & evidence
- ORD record
- ord-b5f05949fedc414ab2b3a2467e2f461d
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321769B2
Linked notes
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