2-Benzylsuccinic anhydride, DL- → HCID 18444351, compound

HRID 459767Notes

Reaction equation

HRID 459767 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:28]1[CH2:32][C:31](=[O:33])[O:30][C:29]1=[O:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[CH2:21]([CH:28]([CH2:32][C:31]([NH:1][C:2]1[CH:3]=[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:17]=[CH:18][C:19]=1[F:20])=[O:33])[C:29]([OH:34])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 38302862-Benzylsuccinic anhydride, DL-HCID 184443734-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one

Product 1

HCID 18444351HCID 18444351, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one (0.135 g, 0.5 mmol; prepared in a manner similar to that described in Example 23), 3-benzyldihydrofuran-2,5-dione (0.095 g, 0.5 mmol) and toluene (8 ml) was heated under reflux for 1 hour, allowed to stand at ambient overnight, then heated under reflux for a further 6.5 hours and allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with hexane (10 ml) and dried in vacuo to give 2-benzyl-N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]succinamic acid (0.156 g) as an off white solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 2.2–2.95 (m 5H) (—CH2CH(CO2H)CH2Ph), 4.2 (s, 2H) (ArCH2—), 6.9–7.25 (m, 7H) (7×ArH), 7.6–7.9 (m, 4H) (4×ArH), 8.15 (d, 1H) (ArH), 9.65 (s, 1H) (chain CONH), 12.2 (s, 1H) (—CO2H), 12.5 (s, 1H) (ring CONH).

Workup

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 1 hour
  4. temperatureheated
  5. temperatureunder reflux for a further 6.5 hours
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with hexane (10 ml)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d9832e9728014fb9ac1b494119dc5c9f
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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