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Sodium Hydroxide → 2-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidine-1-sulfonyl}-ethanol

HRID 708138
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Reaktionsgleichung

Reaktionsgleichung von HRID 708138
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[CH:7][C:8]3[O:17][CH2:16][CH2:15][C:14]4[S:13][C:12]([C:18]5[N:19]([CH:23]([CH3:25])[CH3:24])[N:20]=[CH:21][N:22]=5)=[N:11][C:10]=4[C:9]=3[CH:26]=2)[CH2:2]1.Cl[CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31].[OH-:34].[Na+]>C1COCC1>[CH:23]([N:19]1[C:18]([C:12]2[S:13][C:14]3[CH2:15][CH2:16][O:17][C:8]4[CH:7]=[CH:6][C:5]([CH:3]5[CH2:4][N:1]([S:30]([CH2:29][CH2:28][OH:34])(=[O:32])=[O:31])[CH2:2]5)=[CH:26][C:9]=4[C:10]=3[N:11]=2)=[N:22][CH:21]=[N:20]1)([CH3:24])[CH3:25]
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Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 15385Ethanesulfonylchloride, 2-chloro-2×HCID 670505299-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Produkt 1

HCID 582041062-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-9-yl]-azetidine-1-sulfonyl}-ethanolAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 9-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (0.20 g, 0.54 mmol) in dry THF (20 mL) at 0° C. was added 2-chloroethanesulfonyl chloride (65 μL, 0.6 mmol) and the reaction mixture was stirred at RT for 18 hours. The reaction mixture was cooled to 0° C. and a further 2-chloroethanesulfonyl chloride (1304) was added and the reaction mixture was stirred at RT for 18 hours. An aqueous sodium hydroxide solution (8M, 3.38 mL, 27 mmol) was added and the mixture was heated at 40° C. for 18 hours then concentrated in vacuo. The resultant residue was extracted several times with 10% MeOH in DCM and the combined extracts concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 0-20% MeOH in DCM) followed by preparative HPLC (Gemini C18 column, gradient 5-95% MeOH in H2O+0.1% HCO2H) to give 394 (58 mg, 23%). LCMS: RT=8.45 min, [M+H]+=476. 1H NMR δ (ppm) (DMSO-d6, 80° C.): 8.22 (1H, d, J=2.31 Hz), 8.01 (1H, s), 7.33 (1H, dd, J=8.34, 2.39 Hz), 7.08 (1H, d, J=8.32 Hz), 5.81-5.73 (1H, m), 4.53 (2H, s), 4.37 (2H, t, J=5.09 Hz), 4.22 (3H, s), 3.57 (2H, t, J=6.26 Hz), 3.43 (2H, t, J=5.09 Hz), 2.79 (2H, t, J=6.37 Hz), 1.59 (6H, d, J=6.61 Hz). 1 Exchangeable proton not observed

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe reaction mixture was stirred at RT for 18 hours
  3. temperaturethe mixture was heated at 40° C. for 18 hours
  4. concentrationthen concentrated in vacuo
  5. extractionThe resultant residue was extracted several times with 10% MeOH in DCM
  6. concentrationthe combined extracts concentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2, 0-20% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c91b88dfcbf04e68a6173b65d44b1dd1
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09175009B2

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