2-Octenylsuccinic anhydride → 2-{[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}-dec-4-enoic acid

HRID 459761Notes

Reaction equation

HRID 459761 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1.[CH2:21]([CH:29]1[CH2:33][C:32](=[O:34])[O:31][C:30]1=[O:35])[CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1(C)C=CC=CC=1>[F:20][C:19]1[CH:18]=[CH:17][C:4]([CH2:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[NH:8][N:7]=2)=[CH:3][C:2]=1[NH:1][C:32]([CH2:33][CH:29]([CH2:21][CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:30]([OH:35])=[O:31])=[O:34]

Participants

4

Reactant 2

HCID 5345432-Octenylsuccinic anhydrideHCID 184443734-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one

Product 1

HCID 686228092-{[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}-dec-4-enoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one (0.1 g, 0.37 mmol; prepared in a manner similar to that described in Example 23), 3-oct-2-enyldihydrofuran-2,5-dione (0.078 g, 0.37 mmol) and toluene (10 ml) was heated under reflux for 20 hours, then the solvent was removed in vacuo to give crude 2-{[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}dec-4-enoic acid (0.133 g) as an oil which was used without further purification.

Workup

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 20 hours
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f360b6797b8c432eaf38efbfa95c2e32
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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