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 332985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332985
[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-5b79989e47d64634b1c4eb5f7a9e1108
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877922B2

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