Triethylamine → 1-Methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amide

HRID 553497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553497
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH:24][CH3:25])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1.[CH3:26][N:27]1[CH:31]=[C:30]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[N:28]1>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:9][C:10]1[C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:25])[S:32]([C:30]3[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=3)(=[O:34])=[O:33])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 86640208{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt

Produkt 1

HCID 866402101-Methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Add triethylamine (3.403 mL, 24.414 mmol) to a stirring solution of {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt (2.000 g, 6.103 mmol) in dichloromethane (100 mL). Add 1-methyl-1H-pyrazole-4-sulfonyl chloride (1.102 g, 6.103 mmol) at room temperature. Stir at room temperature for 30 min. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate phases and extract the aqueous phase with dichloromethane. Combine the organic phases, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with hexanes:acetone 1:1 to afford the title preparation (1.600 g, 66% yield). MS ES: m/z=399 [M+H]+.

Aufarbeitung

  1. customat room temperature
  2. extractionSeparate phases and extract the aqueous phase with dichloromethane
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the resulting material by silica gel chromatography
  7. washeluting with hexanes:acetone 1:1
  8. customto afford the title
  9. custompreparation (1.600 g, 66% yield)

Quellen und Nachweise

ORD-Eintrag
ord-fd7182ad77e7409db29493bbf1d6fd5c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048884B2

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