2-(Chloroacetyl)thiophene → (3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469472
[Cl:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:20]([O:22][C@@H:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)=[O:21])[C:11]1=2.C(Cl)Cl.CO>C(#N)C>[Cl-:1].[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:20]([O:22][C@@H:23]3[CH:28]4[CH2:27][CH2:26][N+:25]([CH2:2][C:3](=[O:4])[C:5]5[S:6][CH:7]=[CH:8][CH:9]=5)([CH2:30][CH2:29]4)[CH2:24]3)=[O:21])[C:11]1=2

Komponenten

5

Edukt 3

HCID 27579252-(Chloroacetyl)thiopheneHCID 21226129Dichloromethane methanolHCID 58557003(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetate

Produkt 1

HCID 86660328(3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chlorideAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Chloro-1-(thiophen-2-yl)ethanone (36.8 mg, 0.23 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetate (C27) (90 mg, 0.23 mmol) in acetonitrile (3 ml). The reaction was stirred at r.t. overnight. The solvent was removed under vacuum, and the crude product was triturated with Et2O. The compound was first purified by preparative HPLC (Eluent: CH3CN/H2O) and then by flash chromatography (DCM/MeOH=95/5) to obtain (3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (20 mg, 16% yield).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customthe crude product was triturated with Et2O
  3. customThe compound was first purified by preparative HPLC (Eluent: CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-a41e8da4dc46469092f98f14554f707a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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