Triethylamine → {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

HRID 571548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571548
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([B:20]3[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].C(N(CC)CC)C>C(Cl)Cl.Cl.O1CCOCC1>[CH3:27][C:22]1([CH3:28])[C:23]([CH3:25])([CH3:26])[O:24][B:20]([C:18]2[CH:17]=[N:16][N:15]([C:4]3([CH2:3][C:1]#[N:2])[CH2:5][NH:6][CH2:7]3)[CH:19]=2)[O:21]1

Komponenten

6

Edukt 2

HCID 8471TriethylamineHCID 67457197tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Produkt 1

HCID 71143620{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrileAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 3-(cyanomethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (1.5 g, 3.9 mmol) (Example 40, Step 1) in methylene chloride (15 mL) and 4.0 M hydrogen chloride in dioxane (3.9 mL) was stirred at room temperature over weekend. The mixture was treated with triethylamine (1 mL), and the volatiles were removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-5%) to afford the desired product (0.95 g, 85%). LCMS (M+H)+: m/z=289.2.

Aufarbeitung

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-5%)

Quellen und Nachweise

ORD-Eintrag
ord-87ff0e21117d48f588b3022fc8f50c27
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023840B2

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