Potassium Carbonate → N-(2-{7-[(2S)-3-(4-Cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl}ethyl)-1-phenylmethanesulfonamide

HRID 1992398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992398
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:11][CH:10]2[O:12][CH:6]([CH2:7][N:8]([CH2:13][C@H:14]([OH:25])[CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH2:9]2)[CH2:5]1.[C:26]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(N(CC)CC)C.C(#N)C>[C:21]([C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C@@H:14]([OH:25])[CH2:13][N:8]2[CH2:9][CH:10]3[O:12][CH:6]([CH2:5][N:4]([CH2:3][CH2:2][NH:1][S:33]([CH2:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:35])=[O:34])[CH2:11]3)[CH2:7]2)=[CH:24][CH:23]=1)#[N:22]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 685227854-{(2S)-3-[7-(2-Aminoethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile

Produkt 1

HCID 11677749N-(2-{7-[(2S)-3-(4-Cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl}ethyl)-1-phenylmethanesulfonamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

4-{(2S)-3-[7-(2-Aminoethyl)-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]-2-hydroxypropoxy}benzonitrile (0.096 g, 0.28 mmol; see step Preparation A above) was dissolved in a 1:2 ratio of DCM:acetonitrile (3 mL). Triethylamine (0.17 g, 1.68 mmol) was added, followed by phenylmethanesulfonyl chloride (0.068 g, 0.36 mmol). The mixture was stirred at room temperature overnight with K2CO3 (0.38 g, 2.77 mmol) to ensure that the free base of triethylamine was in the reaction mixture. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. Purification by preparative HPLC gave 0.1 g (72%) of the title compound.

Aufarbeitung

  1. customstep Preparation A above)
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3d2dee7074094c1bae4eecfbea76a7fc
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648985B2

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