Potassium Carbonate → (S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

HRID 1483975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483975
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9](=[O:20])OC2C=CC([N+]([O-])=O)=CC=2)=[CH:3][CH:2]=1.Cl.[NH2:22][C:23]1[C:24]2[C:34]([O:35][CH2:36][C@H:37]3[CH2:42][CH2:41][CH2:40][NH2+:39][CH2:38]3)=[CH:33][CH:32]=[CH:31][C:25]=2[NH:26][S:27](=[O:30])(=[O:29])[N:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:22][C:23]1[C:24]2[C:34]([O:35][CH2:36][C@H:37]3[CH2:42][CH2:41][CH2:40][N:39]([C:9]([NH:8][CH2:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:20])[CH2:38]3)=[CH:33][CH:32]=[CH:31][C:25]=2[NH:26][S:27](=[O:29])(=[O:30])[N:28]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 86714280(S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochlorideHCID 867143034-Nitrophenyl pyridin-4-ylmethylcarbamate

Produkt 1

HCID 73213731(S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-nitrophenyl (pyridin-4-ylmethyl)carbamate (Example 27d, 27.3 mg, 100 umol), (S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochloride (Example 2a, 34.6 mg, 0.10 mmol) and K2CO3 in DMF (1 mL) was stirred at room temperature overnight. The resulting mixture was filtered and purified by preparative HPLC (10-90% acetonitrile in water) to provide the title product as a white solid. MS=445 (MH+).

Aufarbeitung

  1. filtrationThe resulting mixture was filtered
  2. custompurified by preparative HPLC (10-90% acetonitrile in water)

Quellen und Nachweise

ORD-Eintrag
ord-6f67098e1db04cff95145409e0632822
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09420814B2

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