Diisopropylethylamine → HCID 67201273, Verbindung

HRID 550606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550606
Cl.[CH2:2]([O:4][C:5]([N:7]1[C:15]([NH2:16])=[C:10]2[CH2:11][NH:12][CH2:13][CH2:14][C:9]2=[N:8]1)=[O:6])[CH3:3].C(N(CC)C(C)C)(C)C.[F:26][C:27]1[CH:28]=[C:29]([S:34](Cl)(=[O:36])=[O:35])[CH:30]=[C:31]([F:33])[CH:32]=1>ClCCl>[CH2:2]([O:4][C:5]([N:7]1[C:15]([NH2:16])=[C:10]2[CH2:11][N:12]([S:34]([C:29]3[CH:28]=[C:27]([F:26])[CH:32]=[C:31]([F:33])[CH:30]=3)(=[O:36])=[O:35])[CH2:13][CH2:14][C:9]2=[N:8]1)=[O:6])[CH3:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27740583,5-Difluorobenzenesulfonyl chlorideHCID 67202227HCID 67202227, Verbindung

Produkt 1

HCID 67201273HCID 67201273, VerbindungAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 3-amino-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-2-carboxylic acid ethyl ester hydrochloride (36.2 g, 127.8 mmol) in anhydrous dichloromethane (1 L), at 0°-5° C., N,N-diisopropylethylamine (111.3 mL, 639 mmol) was added. To the resulting solution, 3,5-difluorobenzenesulfonyl chloride (27.17 g, 127.8 mmol) was added portionwise. The mixture was stirred at 0°-5° C. for 1 hour then at room temperature for 3 hours. The organic phase was washed with NaHCO3 saturated solution, water and brine, dried over sodium sulfate filtered and evaporated. The crude, was triturated with diethylether (500 mL) to obtain the title compound as yellowish solid (45.48 g, 92%).

Aufarbeitung

  1. waitat room temperature for 3 hours
  2. washThe organic phase was washed with NaHCO3 saturated solution, water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude, was triturated with diethylether (500 mL)

Quellen und Nachweise

ORD-Eintrag
ord-63dc50912c84462c97fade7b4e80aadd
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947686B2

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