StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trifluoroacetic acid → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-10-(1-isopropylpiperidin-4-ylsulfonyl)-9-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

HRID 1530633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530633
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[C:19]([S:23]([CH:25]5[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]5)=[O:24])[C:20]([CH3:22])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:34]=2)=[N:7][C:6]([CH3:35])=[N:5]1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=[O:37].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[C:19]([S:23]([CH:25]5[CH2:30][CH2:29][N:28]([CH:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]5)(=[O:37])=[O:24])[C:20]([CH3:22])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:34]=2)=[N:7][C:6]([CH3:35])=[N:5]1)([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 665586802-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-10-(1-isopropylpiperidin-4-ylsulfinyl)-9-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Produkt 1

HCID 683130062-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-10-(1-isopropylpiperidin-4-ylsulfonyl)-9-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cooled solution of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-9-(1-isopropylpiperidine-4-sulfinyl)-8-methyl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene 225 (30 mg, 0.061 mmol) in DCM (3 mL) was added TFA (24 μL, 0.306 mmol) followed by a solution of m-CPBA (14 mg, 0.0796 mmol) in DCM (1 mL). The resulting mixture was stirred for 3 h at 0° C. then volatiles were removed under reduced pressure. The crude material was purified by column chromatography (C18, gradient 20-50% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3 in MeOH. The basic fractions were combined and concentrated in vacuo and the resulting residue was purified by column chromatography (Si-PCC, gradient 3-15% MeOH in DCM) affording 243 as a white solid (14 mg, 44%). LCMS: RT 2.83 min [M+H]+ 513.1. 1H NMR (CD3OD, 400 MHz): δ 9.08 (1H, s), 7.76 (1H, s), 7.10 (1H, s), 5.93-5.80 (1H, m), 4.63-4.53 (4H, m), 3.21-3.10 (1H, m), 3.00 (2H, bd, J=11.56 Hz), 2.77-2.67 (1H, m), 2.64 (3H, s), 2.37 (3H, s), 2.24 (2H, t, J=12.17 Hz), 1.97 (2H, d, J=12.67 Hz), 1.87-1.74 (2H, m), 1.56 (6H, d, J=6.65 Hz), 1.04 (6H, d, J=6.56 Hz)

Aufarbeitung

  1. customwere removed under reduced pressure
  2. customThe crude material was purified by column chromatography (C18, gradient 20-50% MeOH in 0.5% TFA/H2O)
  3. washThe cartridge was washed with MeOH
  4. washthe product eluted with 0.5M NH3 in MeOH
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified by column chromatography (Si-PCC, gradient 3-15% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-9d425306e4644963b0fb011bb742514c
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090628B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion