Triethylamine → N-(1-(4-(4-Fluorophenyl)phthalazin-1-yl)piperidin-4-yl)benzamide hydrochloride

HRID 1012964

Reaktionsgleichung

Reaktionsgleichung von HRID 1012964
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:3]=1.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:21][CH2:20]1.C(N(CC)CC)C>CN(C)C=O>[ClH:1].[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([N:19]3[CH2:24][CH2:23][CH:22]([NH:25][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:21][CH2:20]3)=[N:3][N:4]=2)=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 118120N-4-PiperidylbenzamideHCID 21152391-Chloro-4-(4-fluorophenyl)phthalazine

Produkt 1

HCID 66971348N-(1-(4-(4-Fluorophenyl)phthalazin-1-yl)piperidin-4-yl)benzamide hydrochlorideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Combine 1-chloro-4-(4-fluorophenyl)phthalazine (150 mg, 0.58 mmol), N-(piperidin-4-yl)benzamide (178 mg, 0.87 mmol), triethylamine (0.404 mL, 2.9 mmol) and dimethylformamide (1 mL) at room temperature. Heat to 100° C. and stir overnight. Pour the crude reaction mixture onto a strong cation exchange Phenomenex Strata® SCX (55 μm, 70 Å) 10 g/60 mL column (with a benzene sulfonic acid functional group). Elute the desired product with 2 N methanolic ammonia (40 mL) and concentrate. Purify the residue by flash chromatography (20-30% [10% 2 N methanolic ammonia in ethyl acetate] in hexane). Add 1 N hydrochloric acid in diethyl ether to a solution of the isolated product in dichloromethane/methanol and remove the solvents under a stream of nitrogen gas to yield the title compound as a solid (137 mg, 51%). ES/MS m/z 427.2 (M+1).

Aufarbeitung

  1. customat room temperature
  2. additionPour the crude
  3. customreaction mixture onto a strong cation exchange Phenomenex Strata® SCX (55 μm, 70 Å) 10 g/60 mL column (with a benzene sulfonic acid functional group)
  4. washElute the desired product with 2 N methanolic ammonia (40 mL)
  5. concentrationconcentrate
  6. customPurify the residue by flash chromatography (20-30% [10% 2 N methanolic ammonia in ethyl acetate] in hexane)
  7. additionAdd 1 N hydrochloric acid in diethyl ether to a solution of the isolated product in dichloromethane/methanol
  8. customremove the solvents under a stream of nitrogen gas

Quellen und Nachweise

ORD-Eintrag
ord-f61117c87c1a4e7ab26889edf29239e0
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981892B2

Verknüpfte Notizen

Wird geladen…