Diisopropylethylamine → HCID 67201273, Verbindung

HRID 1921093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921093
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 satured 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 satured 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-77258f2fc8d943e99bba2a39a5220a79
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173659B2

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