Triethylamine → HCID 178454305, Verbindung

HRID 1247789

Reaktionsgleichung

Reaktionsgleichung von HRID 1247789
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]([CH2:13][CH2:14][OH:15])[C:11]=1[NH2:12].C(N(CC)CC)C.[C:23]([O:27][C:28]([NH:30][C:31]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=NS(C(F)(F)F)(=O)=O)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[NH2:12][C:11]1[N:10]([CH2:13][CH2:14][OH:15])[N:9]=[CH:8][C:7]=1[NH:6][C:31]([NH:30][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])=[N:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 36945701,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidineHCID 116731484,5-Diamino-1-(2-hydroxyethyl)pyrazole sulfate

Produkt 1

HCID 178454305HCID 178454305, VerbindungAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of 4,5-diamino-1-(2-hydroxyethyl)pyrazole sulfuric acid salt (50.0 g) in chloroform (500 ml) were added 4-(dimethylamino)pyridine (2.54 g), triethylamine (116 ml) and 1,3-bis(tert-butoxycarbonyl)-2-(trifluoromethanesulfonyl)guanidine (106 g). The mixture was stirred under reflux for 2 hours. After cooling on an ice bath, the reaction mixture was washed successively with water, 4% aqueous citric acid solution, water and aqueous sodium hydrogen carbonate solution. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with a mixed solvent of ethyl acetate (50 ml) and diethyl ether (200 ml) to give 5-amino-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-1-(2-hydroxyethyl)pyrazole (50 g) as a solid.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling on an ice bath
  3. washthe reaction mixture was washed successively with water, 4% aqueous citric acid solution, water and aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with a mixed solvent of ethyl acetate (50 ml) and diethyl ether (200 ml)

Quellen und Nachweise

ORD-Eintrag
ord-b80e7dc6a372410d80543c891bdf48e2
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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