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

HRID 459764Notes

Reaction equation

HRID 459764 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][CH:33]([CH2:37][CH:38]=[CH:39][CH2:40][CH2:41][CH3:42])[C:34]([OH:36])=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][CH:33]([CH2:37][CH:38]=[CH:39][CH2:40][CH2:41][CH3:42])[C:34]1=[O:36]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 686238932-{[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}oct-4-enoic acid

Product 1

HCID 686243611-[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-hex-2-enylpyrrolidine-2,5-dioneYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.047 g, 0.15 mmol) and diisopropylethylamine (0.043 g, 0.25 mmol) were added sequentially at ambient temperature to a stirred solution 2-{[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}oct-4-enoic acid (0.051 g, 0.11 mmol) in dimethylformamide (2 ml), the mixture was stirred at ambient temperature for 48 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]-3-hex-2-enylpyrrolidine-2,5-dione (0.029 g) as an off-white solid, m.pt. 146–149° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 0.8–1.0 (m, 3H) (CH3), 1.2–1.4 (m, 2H) (—CH2CH3), 1.9–2.1 (m, 2H) (—CH2CH2CH3), 2.3–2.5 (m, 2H) (—CH2CH═CH—), 2.5–2.6 (m, 1H) (ring CH), 2.8–3.0 and 3.0–3.2 (2×m, 2H) (ring CH2), 4.4 (s, 2H) (ArCH2—), 5.25–5.45 and 5.45–5.7 (2×m, 2×1H) (—CH═CH—) 7.2–7.3 (m, 1H) (ArH), 7.3–7.5 (m, 1H) (ArH), 7.5–7.6 (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)+. 434, 95.8% purity.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-6e73030d9d014a1cb98c2bf28e4dc703
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

Loading…