2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride → 1-(Pyridin-4-yl)-4-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylaminomethyl)piperidine-4-carboxylic acid ethyl ester

HRID 412608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412608
Br.Br.[CH2:3]([O:5][C:6]([C:8]1([CH2:20][NH2:21])[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4].Cl[S:23]([C:26]1[CH:35]=[C:34]2[C:29]([CH2:30][CH2:31][N:32]([C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])[CH2:33]2)=[CH:28][CH:27]=1)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH2:3]([O:5][C:6]([C:8]1([CH2:20][NH:21][S:23]([C:26]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][N:32]([C:36](=[O:41])[C:37]([F:40])([F:38])[F:39])[CH2:33]3)=[CH:28][CH:27]=2)(=[O:24])=[O:25])[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH3:4]

Komponenten

4

Edukt 2

HCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 696973274-Aminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrobromide

Produkt 1

HCID 865907251-(Pyridin-4-yl)-4-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-ylsulfonylaminomethyl)piperidine-4-carboxylic acid ethyl esterAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To 4-aminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrobromide (423 mg) were added pyridine (2 ml) and 7-chlorosulfonyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (273 mg), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated and water was added. The mixture was extracted with chloroform and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=4:1) and dried under reduced pressure to give the title compound (222 mg).

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionwater was added
  4. extractionThe mixture was extracted with chloroform
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=4:1)
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-edc995e474914abeab1f7dda054d6543
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562828B1

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