Diisopropylethylamine → 1-(2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)phenyl)piperidine-2,6-dione
Reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:28])[NH:20][N:19]=2)=[CH:13][C:12]=1[NH:29][C:30]([CH2:32][CH2:33][CH2:34][C:35]([OH:37])=O)=[O:31]>CN(C)C=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:28])[NH:20][N:19]=2)=[CH:13][C:12]=1[N:29]1[C:30](=[O:31])[CH2:32][CH2:33][CH2:34][C:35]1=[O:37]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.087 g, 0.27 mmol) and diisopropylethylamine (0.079 ml, 0.46 mmol) were added sequentially at ambient temperature to a stirred solution of 4-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]butyric acid (0.08 g, 0.21 mmol) in dimethylformamide (2 ml), the mixture was stirred at ambient temperature for 50 hours, then it was added dropwise to ice-cold water (10 ml). The resulting solid was collected by filtration and dried in vacuo to give 1-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]piperidine-2,6-dione (0.05 g) as a white solid, m.pt. 259–263° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 1.8–2.1 (m, 2H) (—CH2CH2CH2—), 2.7–2.9 (m, 4H) (—CH2CH2CH2—) 4.35 (s, 2H) (ArCH2—), 7.1–7.35 (m, 2H) (2×ArH), 7.4–7.5 (m, 1H) (ArH), 7.8–8.05 (m, 3H) (3×ArH), 8.3 (d, 1H) (ArH), 12.65 (s, 1H) (CONH); m/z (M+H)+ 366, 100% purity.
Workup
- filtrationThe resulting solid was collected by filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9db3ac586ca94e9fa135330e937a761e
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196085B2
Reaction notes
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