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Water → HCID 178433404, Verbindung

HRID 1661072
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1661072
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:7]1([CH2:11][CH2:10][NH:9][CH2:8]1)[CH2:6][CH2:5]2.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].O.[Cl:24][CH2:25][CH2:26][CH2:27][S:28][C:29]1[N:33]=[C:32]([C:34]2[O:38][CH:37]=[N:36][C:35]=2[CH3:39])[NH:31][N:30]=1>CN(C=O)C>[ClH:24].[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:7]1([CH2:11][CH2:10][N:9]([CH2:25][CH2:26][CH2:27][S:28][C:29]3[NH:30][N:31]=[C:32]([C:34]4[O:38][CH:37]=[N:36][C:35]=4[CH3:39])[N:33]=3)[CH2:8]1)[CH2:6][CH2:5]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 962WaterHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 592339285-Bromo-2,3-dihydrospiro[1H-indene-1,3′-pyrrolidine]HCID 67430173HCID 67430173, Verbindung

Produkt 1

HCID 178433404HCID 178433404, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-bromo-2,3-dihydrospiro[indene-1,3′-pyrrolidine] (Prep4, 0.04 g, 0.159 mmol) in dry DMF (1 ml), 3-[(3-chloropropyl)thio]-5-(4-methyl-1,3-oxazol-5-yl)-1H-1,2,4-triazole (reference procedure for preparation described in WO05/080382, 0.058 g, 0.213 mmol) was added. Then, K2CO3 (0.029 g) and NaI (0.028 g) were added and the mixture was heated at 80° C. for 24 hours. Water was then added and the solution was extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a silica SPE cartridge eluting with dichloromethane/methanol from 100/0 to 98/to obtain 0.036 g of the title compound as free base. To a solution of this material in dichloromethane (1 mL) was added 0.073 mL of HCl (1M in Et2O), the solvent was evaporated in vacuo and the material thus obtained triturated with Et2O to give 32 mg of the title compound as a white slightly hygroscopic solid.

Aufarbeitung

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by a silica SPE cartridge
  7. washeluting with dichloromethane/methanol from 100/0 to 98/to

Quellen und Nachweise

ORD-Eintrag
ord-750b14ebc5f04c019266bfdf4b647ef7
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08030322B2

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