Diisopropylethylamine → 1-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-methylpyrrolidine-2,5-dione

HRID 459770Notes

Reaction equation

HRID 459770 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](=[O:37])[CH2:31][CH:32]([CH3:36])[C:33](O)=[O:34]>CC(N(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:37])[CH2:31][CH:32]([CH3:36])[C:33]1=[O:34]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 18444382N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-methylsuccinamic acid

Product 1

HCID 184443351-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-methylpyrrolidine-2,5-dioneYield 68.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (1.09 g, 3.4 mmol) and diisopropylethylamine (0.98 g, 5.7 mmol) were added sequentially to a stirred solution of N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-methylsuccinamic acid (1 g, 2.6 mmol) in dimethylacetamide (5 ml), the mixture was stirred at ambient temperature for 15 minutes, then it was poured onto water (50 ml) and allowed to stand at ambient temperature for 20 hours. The resulting solid was collected by filtration, washed with hexane (20 ml) and dried in vacuo to give 1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-methylpyrrolidine-2,5-dione (0.654 g) as a beige solid, m.pt. 171–172° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 1.4 (d, 3H) (CH3), 2.6–2.7 (m, obscured by DMSO signal, 1H) (—CHMe-), 3.05–3.3 (m, 2H) (—CH2CHMe-), 4.5 (s, 2H) (ArCH2—), 7.3–7.55 (m, 2H) (2×ArH), 7.6–7.7 (m, 1H) (ArH), 7.9–8.2 (m, 3H) (3×ArH), 8.4 (d, 1H) (ArH), 12.8 (s, 1H) (CONH); m/z (M+H)+ 366, 98% purity.

Workup

  1. additionit was poured onto water (50 ml)
  2. waitto stand at ambient temperature for 20 hours
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with hexane (20 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bd451a24227c4d99b5aabedee1b85da5
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

Loading…