2,5-Furandione, 3-(2-hexen-1-yl)dihydro- → 2-{[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}oct-4-enoic acid

HRID 459763Notes

Reaction equation

HRID 459763 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:27]1[CH2:31][C:30](=[O:32])[O:29][C:28]1=[O:33])[CH:22]=[CH:23][CH2:24][CH2:25][CH3:26]>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]([CH2:31][CH:27]([CH2:21][CH:22]=[CH:23][CH2:24][CH2:25][CH3:26])[C:28]([OH:33])=[O:29])=[O:32]

Participants

4

Reactant 2

HCID 1120552,5-Furandione, 3-(2-hexen-1-yl)dihydro-HCID 184443734-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one

Product 1

HCID 686238932-{[2-Fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}oct-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-hex-2-enyldihydrofuran-2,5-dione (0.068 g, 0.37 mmol) and toluene (10 ml) was heated under reflux for 20 hours, then the resulting solid was collected by filtration from the hot mixture, washed with ethyl acetate (3 ml) and dried in vacuo to give 2-{[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenylcarbamoyl]methyl}oct-4-enoic acid (0.061 g) as an off-white solid, m.pt. 179–181° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 0.7–0.9 (t, 3H) (CH3), 1.1–1.35 (m, 2H) (—CH2CH3), 1.75–2.0 (m, 2H) (—CH2CH2CH3), 2.0–2.3 (m, 2H) (—CH2CH═CH—), 2.3–2.8 (2×m obscured by DMSO signal, 2H+1H) (—CH2CH(CO2H)CH2—), 4.2 (s, 2H) (ArCH2—), 5.15–5.5 (m, 2H) (—CH═CH—) 6.9–7.2 (m, 2H) (2×ArH), 7.65–8.0 (m, 4H) (4×ArH), 8.2 (d, 1H) (ArH), 12.1 (br s, 1H) (CO2H), 12.6 (s, 1H) (CONH); m/z (M+H)+. 452, 93.7% purity.

Workup

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 20 hours
  4. filtrationthe resulting solid was collected by filtration from the hot mixture
  5. washwashed with ethyl acetate (3 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c97c5698f9364b4186650ecea99884b8
Source dataset
uspto-grants-2007_03
Patent number
US07196085B2

Reaction notes

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