Toluene → N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-methylsuccinamic acid

HRID 459769

反応式

HRID 459769 の反応式
[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.[CH3:21][CH:22]1[CH2:26][C:25](=[O:27])[O:24][C:23]1=[O:28].C1(C)C=CC=CC=1>O>[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:25](=[O:27])[CH2:26][CH:22]([CH3:21])[C:23]([OH:28])=[O:24]

参加物

5

反応物 3

HCID 1140TolueneHCID 20051Methylsuccinic anhydrideHCID 184443734-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one

生成物 1

HCID 18444382N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-methylsuccinamic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A stirred mixture of 4-(3-amino-4-fluorobenzyl)-2H-phthalazin-1-one (2.02 g, 7.5 mmol; prepared in a manner similar to that described in Example 23), 3-methyldihydrofuran-2,5-dione (0.856 g, 7.5 mmol) and toluene (100 ml) was heated under reflux for 2.5 hours (for the first 30 minutes of this period, traces of water in the mixture were removed by azeotropic distillation). The resulting solid was collected by filtration from the hot mixture, washed with toluene (20 ml) and dried in vacuo to give N-[2-fluoro-5-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-methylsuccinamic acid (1.91 g) as an off-white solid, m.pt. 140–144° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 0.95 (d, 3H) (CH3), 2.2–2.6 (m, 3H) (—CH2CHMe-), 4.1 (s, 2H) (ArCH2—), 6.9–7.2 (m, 2H) (2×ArH), 7.6–7.9 (m, 4H) (4×ArH), 8.1 (d, 1H) (ArH), 9.55 (s, 1H) (chain CONH), 12.0 (br s, 1H) (CO2H), 12.5 (s, 1H) (ring CONH); m/z (M+H)+ 384, 100% purity.

後処理

  1. customprepared in a manner similar to
  2. temperaturewas heated
  3. temperatureunder reflux for 2.5 hours (for the first 30 minutes of this period
  4. customwere removed by azeotropic distillation)
  5. filtrationThe resulting solid was collected by filtration from the hot mixture
  6. washwashed with toluene (20 ml)
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-b7b52a9354ba48a7bcbbaae69407a098
出典データセット
uspto-grants-2007_03
特許番号
US07196085B2

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