N-(tert-Butoxycarbonyl)-1,2-phenylenediamine → tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate

HRID 1984774

Reaktionsgleichung

Reaktionsgleichung von HRID 1984774
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][N:18]=1>C(Cl)Cl>[Cl:16][C:17]1[N:18]=[CH:19][C:20]([C:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:22])=[CH:24][CH:25]=1

Komponenten

4

Edukt 2

HCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 27821656-Chloronicotinoyl Chloride

Produkt 1

HCID 57717462tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of t-butyl (2-aminophenyl)carbamate A1 (10 g, 48.0 mmol) in CH2Cl2 (200 mL) was added 6-chloronicotinoyl chloride (8.5 g, 48.0 mmol). The reaction mixture was concentrated after 2 hours of stirring at room temperature and purified by flash chromatography (10-75% EtOAc/hexanes) to give the Boc-protected nicotinamide B1 confirmed by MS (ESI+): cal'd [M+Na]+370.1, obs'd 370.1.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated after 2 hours
  2. custompurified by flash chromatography (10-75% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-699ff260eaa540d5b6a141cb45d25f16
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544695B2

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