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2-Methylpyridine → N-[2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetyl]sulfamic acid

HRID 1271313
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1271313
N1C=CC=CC=1C.Cl[S:9]([OH:12])(=[O:11])=[O:10].[C:13]1([C:19]2[N:20]=[CH:21][C:22]([N:31]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]([NH2:43])=[O:42])[CH:32]([CH3:34])[CH3:33])=[N:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl.ClCCl>[C:13]1([C:19]2[N:20]=[CH:21][C:22]([N:31]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]([NH:43][S:9](=[O:11])(=[O:10])[OH:12])=[O:42])[CH:32]([CH3:34])[CH3:33])=[N:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 79752-MethylpyridineHCID 24638Chlorosulfonic acidHCID 184526472-[4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy]acetamide

Produkt 1

HCID 18452623N-[2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetyl]sulfamic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-Dichloroethane
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Under an argon atmosphere, a solution of 1.443 g of 2-picoline in 1.7 ml of 1,2-dichloroethane was cooled to −10° C. A solution of chlorosulfonic acid in 3.5 ml of 1,2-dichloroethane was added dropwise at 0° C. or lower and, after stirring for 15 minutes, 712 mg of 2-[4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy]acetamide was added. The reaction solution was heated to 75° C. and air-cooled to room temperature after stirring for 2 hours. The reaction solution was diluted with dichloromethane and then washed in turn with an aqueous 0.6M sodium hydrogen sulfate and water. The reaction solution was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 798 mg of N-[2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetyl]sulfamic acid.

Aufarbeitung

  1. temperatureair-cooled to room temperature
  2. stirringafter stirring for 2 hours
  3. washwashed in turn with an aqueous 0.6M sodium hydrogen sulfate and water
  4. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-499cc722778d4455ab7262954f47a3c4
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07205302B2

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