Phenylsuccinic Anhydride → N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-phenylsuccinamic acid

HRID 459759Notes

Reaction equation

HRID 459759 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.[C:21]1([CH:27]2[CH2:31][C:30](=[O:32])[O:29][C:28]2=[O:33])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>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:30](=[O:32])[CH2:31][CH:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:28]([OH:33])=[O:29]

Participants

4

Reactant 2

HCID 136911Phenylsuccinic AnhydrideHCID 184443734-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one

Product 1

HCID 18444383N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-phenylsuccinamic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one (0.7 g, 2.6 mmol; prepared in a manner similar to that described in Example 23), 3-phenyldihydrofuran-2,5-dione (0.458 g, 2.6 mmol) and toluene (35 ml) was heated under reflux for 2 hours then allowed to cool to ambient temperature. The resulting solid was collected by filtration, washed with ethyl acetate (3 ml) and dried in vacuo to give N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-phenylsuccinamic acid (0.775 g) as an off-white solid, m.pt. 180–183° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 2.7–2.9 (m, 1H) (—CHHCHPh—), 3.1–3.3 (m, 1H) (—CHHCHPh—), 4.0–4.1 (m, 1H) (—CHPh—) 4.3 (s, 2H) (ArCH2—), 7.1–7.3 (m, 2H) (2×ArH), 7.3–7.5 (m, 5H) (5×ArH), 7.8–8.0 (m, 4H) (4×ArH), 8.3 (d, 1H) (ArH), 9.75 (s, 1H) (chain CONH), 12.5 (br s, 1H) (—CO2H), 12.65 (s, 1H) (ring CONH) ; m/z (M+H)+. 446, 100% purity.

Workup

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 2 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with ethyl acetate (3 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-af6273a7439847ea825e055a9fefe688
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

Loading…