Water → 6-Chloro-4-(3-iodobenzylamino)nicotinamide

HRID 513280

Reaktionsgleichung

Reaktionsgleichung von HRID 513280
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[C:4]([Cl:11])[CH:3]=1.[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17].CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1.CCOC(C)=O>[Cl:11][C:4]1[CH:3]=[C:2]([NH:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([I:12])[CH:14]=2)[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 970123-IodobenzylamineHCID 6000444,6-Dichloronicotinamide

Produkt 1

HCID 866645466-Chloro-4-(3-iodobenzylamino)nicotinamideAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of 4,6-dichloronicotinamide (400 mg, 2.09 mmol), 3-iodobenzylamine (0.285 mL, 2.13 mmol) and DIEA (0.500 mL, 2.87 mmol) in NMP (5 mL) was stirred at 90 C for 48 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-100% EtOAc in hexane to give 6-chloro-4-(3-iodobenzylamino)nicotinamide as a solid (266 mg).

Aufarbeitung

  1. customOrganic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column
  5. washeluted with 0-100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4921231e157b48ab82f419ed3f359d14
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102625B2

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