Sodium Chloride → HCID 18444338, compound

HRID 459773Notes

Reaction equation

HRID 459773 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][N:33]([CH3:38])[CH2:34][C:35]([OH:37])=O)=[O:31].[Cl-].[Na+]>CC(N(C)C)=O.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][N:33]([CH3:38])[CH2:34][C:35]1=[O:37]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 58823955HCID 58823955, compound

Product 1

HCID 18444338HCID 18444338, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

O-Benzotriazol-1-yl-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.108 g, 0.34 mmol) and diisopropylethylamine (0.074 g, 0.57 mmol) were added sequentially at ambient temperature to a stirred solution of N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoylmethyl]-N-methylglycine (0.103 g, 0.26 mmol) in dimethylacetamide (1 ml), the mixture was stirred at ambient temperature for 1 hour, then it was diluted with water (10 ml). Sodium chloride (1 g) was added, the mixture was stirred at ambient temperature for 30 minutes, then the resulting solid was collected by filtration, washed with water (1 ml) and dried in vacuo to give 1-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-4-methylpiperazine-2,6-dione (0.071 g) as a beige solid, m.pt. 205–208° C.; 250 MHz 1H-nmr (CDCl3) δ (ppm): 2.4 (s, 3H) (CH3), 3.5 (q, 4H) (2×CH2), 4.25 (s, 2H) (ArCH2—), 7.1 (m, 2H) (2×ArH), 7.25 (m, 1H) (ArH), 7.7–7.85 (m, 3H) (3×ArH), 8.4 (m, 1H) (ArH), 10.35 (s, 1H) (CONH); m/z (M+H)+. 381, 100% purity.

Workup

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

Sources & evidence

ORD record
ord-1d12432926ee4cc29691fecaa0a2e6d5
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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