Diisopropylethylamine → N-diaminomethylene-3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzamide

HRID 2211025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2211025
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH:15]1[NH2:27])[C:8]([OH:10])=O)(=[O:4])=[O:3].CS(C1C=C(C=CC=1F)C(OC)=O)(=O)=O.C(C1CCN(N)CC1)(OC(C)(C)C)=O.[Cl-].C[N+]1C=CC=CC=1Cl.[Cl-].[NH2:67][C:68]([NH2:70])=[NH2+:69].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[NH2:69][C:68]([NH2:70])=[N:67][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH:15]2[NH2:27])=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=1

Komponenten

8

Edukt 6

HCID 81531DiisopropylethylamineHCID 5460839Carbamimidoylazanium ChlorideHCID 10752025Methyl 4-Fluoro-3-(methylsulfonyl)benzoateHCID 117449626-chloro-N-methylpyridinium chlorideHCID 21899493Tert-butyl 1-aminopiperidine-4-carboxylateHCID 677890783-methylsulphonyl-4-(4-BOC-aminopiperidino)benzoic acid

Produkt 1

HCID 70199108N-diaminomethylene-3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

1.0 g of 3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzoic acid [obtainable by reacting methyl 3-methylsulphonyl-4-fluorobenzoate with 4-BOC-aminopiperidine and subsequently hydrolyzing the product to give the free acid] is dissolved in 15 ml of 1-methylpyrrolidone, and 0.67 g of 1-methyl-2-chloropyridinium chloride is added to this solution, which is stirred for 15 min. 0.9 g of guanidinium chloride and 2.6 ml of diisopropylethylamine are then added and the mixture is stirred at room temperature for 1 hr. After customary working-up, and after chromatography on silica gel (flash process, ethylacetate/10% methanol), N-diaminomethylene-3-methylsulphonyl-4-(4-BOC-aminopiperidino)benzamide is obtained.

Aufarbeitung

  1. customto give the free acid]
  2. stirringthe mixture is stirred at room temperature for 1 hr

Quellen und Nachweise

ORD-Eintrag
ord-e67c2546347d447192afd83a9ba9cf62
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05461066

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