m-Chloroperbenzoic acid → HCID 10295871, Verbindung

HRID 1373814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373814
[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH2:1]([NH:5][C:6]1[N:11]2[N:12]=[C:13]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([S:21]([CH3:22])=[O:38])[N:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acid2×HCID 69450353N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine

Produkt 1

HCID 10295871HCID 10295871, VerbindungAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a cold (0° C.) solution of N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (1.51 g, 3.7 mmol) in 50 mL chloroform was added m-chloroperbenzoic acid (0.87 g, 70–75%, 3.7 mmol). The reaction was allowed to warm to rt. After stirring for 5 h, another 0.2 g m-chloroperbenzoic acid was added and the reaction was stirred for 15 min. The reaction was diluted with aqueous sodium bicarbonate and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate and concentrated. The crude product was recrystallized from ethyl acetate-hexanes to afford N-butyl-2-(4-fluorophenyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-7-amine (0.95 g, 60%) as an orange solid. 1H NMR (CDCl3): δ 8.40 (broad, 1H), 7.99 (d, 1H), 7.58 (m, 2H), 7.45 (t, 1H), 7.20 (t, 2H), 6.94 (d, 1H), 6.13 (d, 1H), 6.10 (broad, 1H), 3.38 (m, 2H), 2.98 (s, 3H), 1.79–1.42 (m, 4H), 0.97 (t, 3H); MS m/z 422 (M−1).

Aufarbeitung

  1. stirringthe reaction was stirred for 15 min
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d972d2e3392c4dd092a9edf420c2d185
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163940B2

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