Diisopropylethylamine → HCID 18444363, compound

HRID 459768Notes

Reaction equation

HRID 459768 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([CH:17]([CH2:21][C:22]([NH:24][C:25]1[CH:30]=[C:29]([CH2:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:35](=[O:42])[NH:34][N:33]=2)[CH:28]=[CH:27][C:26]=1[F:43])=[O:23])[C:18]([OH:20])=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C)C=O>[CH2:10]([CH:17]1[CH2:21][C:22](=[O:23])[N:24]([C:25]2[CH:30]=[C:29]([CH2:31][C:32]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:35](=[O:42])[NH:34][N:33]=3)[CH:28]=[CH:27][C:26]=2[F:43])[C:18]1=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 18444351HCID 18444351, compound

Product 1

HCID 18444363HCID 18444363, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.14 g, 0.44 mmol) and diisopropylethylamine (0.097 g, 0.44 mmol) were added sequentially at ambient temperature to a stirred solution of 2-benzyl-N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]succinamic acid (0.156 g, 0.34 mmol) in dimethylformamide (2 ml), the mixture was stirred at ambient temperature for 3 hours, then it was added dropwise to ice-cold water (10 ml). The mixture was stirred for 30 minutes, then the resulting solid was collected by filtration, washed with water (5 ml) and dried in vacuo to give 3-benzyl-1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]pyrrolidine-2,5-dione (0.120 g) as a white solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 2.6–3.4 (m 5H) (—CH2CH(CO2H)CH2Ph), 4.5 (s, 2H) (ArCH2—), 7.3–7.6 (m, 7H) (7×ArH), 7.6–7.7 (m, 1H) (ArH), 7.9–8.2 (m, 3H) (3×ArH), 8.4 (m, 1H) (ArH), 12.8 (br s, 1H) (CONH); m/z (M+H)+ 442, 96.8% purity.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with water (5 ml)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1167658bd7664ddfa8c3057d30073672
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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