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2-(Benzenesulfonyl)-3-phenyloxaziridine → Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

HRID 472832
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 472832
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C2[O:42]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:18])[C:3]=1[CH:19]([OH:42])[C:20]([O:22][CH3:23])=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86670274Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Produkt 1

HCID 86670273Methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetateAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of methyl 2-(7-chloro-2-(3-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (7.8 g, 22.27 mmol) in THF (40 mL) at −78° C. was added KHMDS (44.5 mL, 22.27 mmol) dropwise over 30 min. The mixture was stirred at −78° C. for 30 min. A solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (8.73 g, 33.4 mmol) in THF (50 mL) was added over 30 min and the reaction mixture was stirred for additional 2 h at −78° C. The reaction mixture was quenched with saturated NH4Cl aqueous solution (40 mL). The reaction mixture was allowed to warm to room temperature and then diluted with ethyl acetate (200 mL). The organic phase was washed with water and brine and dried with sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (4.2 g, 51.5%). 1H NMR (500 MHz, CHLOROFORM-d) δ 8.05-7.97 (m, 1H), 7.88 (dt, J=6.7, 1.8 Hz, 1H), 7.44-7.38 (m, 2H), 6.93 (s, 1H), 5.76 (s, 1H), 3.84 (s, 3H), 2.62 (s, 3H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for additional 2 h at −78° C
  2. customThe reaction mixture was quenched with saturated NH4Cl aqueous solution (40 mL)
  3. temperatureto warm to room temperature
  4. additiondiluted with ethyl acetate (200 mL)
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. customThe solvent was evaporated
  8. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ca834c3a519346b095fe9bb2beaaa7dd
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08633200B2

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