N-bromobutanimide → 5-Bromo-6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide

HRID 2044061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2044061
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)[N:3]=1.C1C(=O)N([Br:33])C(=O)C1.OS([O-])=O.[Na+]>C(#N)C.C(OCC)(=O)C>[Br:33][C:10]1[C:2]([Cl:1])=[N:3][C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[O:19])=[CH:16][CH:17]=2)=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]

Komponenten

6

Edukt 3

HCID 67184N-bromobutanimideHCID 23665763Sodium BisulfiteHCID 574896016-Chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide

Produkt 1

HCID 574896165-Bromo-6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamideAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide (500 mg, 1.385 mmol) and NBS (250 mg, 1.4 mmol) in acetonitrile (10 mL) was stirred at overnight. The reaction mixture was treated with 1M NaHSO3 and stirred at rt for 2 h. Next, the reaction mixture was diluted with ethyl acetate and the precipitate filtered to give a solid. The organic layer of the filtrate was separated and concentrated to an additional amount of solid. The above solids were combined and triturated with 250 mL of MeOH/CH2Cl2 (˜1:1 ratio) to give 235 mg of 5-bromo-6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide as a grey solid. LCMS: (M+H)+=338.80, 440.83, 442.87 (Br, Cl pattern). 1H NMR (400 MHz, methanol-d3-MIX) δ ppm 8.38 (1H, s), 7.77 (2H, d, J=8.35 Hz), 7.42 (2H, d, J=8.79 Hz), 3.69 (8H, br. s.).

Aufarbeitung

  1. stirringstirred at rt for 2 h
  2. filtrationthe precipitate filtered
  3. customto give a solid
  4. customThe organic layer of the filtrate was separated
  5. concentrationconcentrated to an additional amount of solid
  6. customtriturated with 250 mL of MeOH/CH2Cl2 (˜1:1 ratio)

Quellen und Nachweise

ORD-Eintrag
ord-a3e815b8d3e747bda3923439036c1aac
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586751B2

Notizen zur Reaktion

Wird geladen…