Triethylamine → N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-4-methylbenzamide

HRID 271827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271827
[CH2:1]([C:8]1[C:9]([CH:18]([NH:22][CH2:23][CH2:24][CH2:25][N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH:19]([CH3:21])[CH3:20])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[CH3:47])[C:41]([Cl:43])=[O:42].C(N(CC)CC)C>C(Cl)Cl>[F:37][C:38]1[CH:39]=[C:40]([CH:44]=[CH:45][C:46]=1[CH3:47])[C:41]([Cl:43])=[O:42].[CH2:1]([C:8]1[C:9]([CH:18]([N:22]([CH2:23][CH2:24][CH2:25][N:26]2[C:27](=[O:36])[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:34]2=[O:35])[C:41](=[O:42])[C:40]2[CH:44]=[CH:45][C:46]([CH3:47])=[C:38]([F:37])[CH:39]=2)[CH:19]([CH3:20])[CH3:21])=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27348753-Fluoro-4-methylbenzoyl chlorideHCID 598361892-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

Produkt 2

HCID 27348753-Fluoro-4-methylbenzoyl chlorideHCID 59836196N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-4-methylbenzamideAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 17 (15 mg, 1 eq.) in CH2Cl2 (1 ml), was added 3-fluoro-4-methyl benzoyl chloride 18 (11 mg, 2 eq.). Benzoyl chloride 18 is prepared using conventional means known in the art. Triethylamine (18 μl, 4 eq.) was then added. The reaction mixture was stirred at room temperature overnight. The reaction was quenched by adding water. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to yield 19 mg of N-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-4-methylbenzamide 19.

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby adding water
  3. washThe organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-96ac661b4d1c4db3b423198ad73142a6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452996B2

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