Water → HCID 18444342, compound

HRID 459751Notes

Reaction equation

HRID 459751 reaction equation
C(N(C(C)C)CC)(C)C.[O:10]=[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:41])[CH2:30][CH:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:32]([OH:34])=O)[CH:25]=[CH:26][CH:27]=2)=[N:13][NH:12]1.O=C1C2C(=CC=CC=2)C(CC2C=C(NC(=O)C(C3C=CC=CC=3)CC(O)=O)C=CC=2)=NN1.O>CN(C)C=O>[O:10]=[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]2[CH:23]=[C:24]([N:28]3[C:29](=[O:41])[CH2:30][CH:31]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:32]3=[O:34])[CH:25]=[CH:26][CH:27]=2)=[N:13][NH:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 18444385HCID 18444385, compoundHCID 18444386HCID 18444386, compound

Product 1

HCID 18444342HCID 18444342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.139 g, 0.429 mmol) and diisopropylethylamine (0.095 g, 0.726 mmol) were added sequentially at ambient temperature to a stirred solution of the above mixture of N-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-phenylsuccinamic acid and N-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenylsuccinamic acid (0.142 g, 0.33 mmol) in dimethylformamide (2 ml), the mixture was stirred at ambient temperature for 3.25 hours and allowed to stand at ambient temperature for 18 hours, then it was added dropwise to water (10 ml). The mixture was stirred at ambient temperature for 30 minutes, then the resulting solid was collected by filtration, washed with water (5 ml) and hexane (10 ml), and dried in vacuo to give 1-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenylpyrrolidine-2,5-dione (0.097 g) as an off-white solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 3.0 (m, 1H) (ring CH), 3.4 (m partially obscured by water peak, 1H) (ring CH), 4.4–4.55 (m, 3H) (ArCH2—+ring CH), 7.25–7.65 (m, 9H) (9×ArH), 7.9–8.15 (m, 3H) (3×ArH), 8.4 (d, 1H) (ArH), 12.8 (s, 1H) (CONH); m/z (M+H)+. 410, 94.2% purity.

Workup

  1. waitto stand at ambient temperature for 18 hours
  2. stirringThe mixture was stirred at ambient temperature for 30 minutes
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed with water (5 ml) and hexane (10 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3700ef4f6c1c4267a82c25f95f760cfb
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

Loading…