Hydrochloric Acid → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothiophene-2-carboxamide hydrochloride

HRID 335596

Reaktionsgleichung

Reaktionsgleichung von HRID 335596
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2].CN(C(ON1N=[N:31][C:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:40](N(CC)C(C)C)(C)[CH3:41].CN(C=O)C.[ClH:54]>C(OCC)C>[ClH:54].[N:30]12[CH2:29][CH2:28][CH:27]([CH2:40][CH2:41]1)[C@@H:26]([NH:31][C:12]([C:10]1[S:11][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][C:8]=3[CH:9]=1)=[O:14])[CH2:25]2

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2389395-Nitro-1-benzothiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 68429753N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothiophene-2-carboxamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

420 mg (1.88 mmol) of 5-nitro-1-benzothiophene-2-carboxylic acid, 374.7 mg (1.88 mmol) of R-3-aminoquinuclidine dihydrochloride, 858.6 mg (2.26 mmol) of HATU, 875.5 mg (6.78 mmol) of N,N-diisopropylethylamine and 2.0 ml of DMF are reacted according to the general procedure (variant B). The resulting precipitate is suspended in 1N HCl in diethyl ether, filtered off, washed twice with dichloromethane and dried under high vacuum. 523 mg (75.6% of theory) of the title compound are obtained.

Aufarbeitung

  1. filtrationfiltered off
  2. washwashed twice with dichloromethane
  3. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-311e9f799bd242469131e8b95a63114f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884017B2

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