Water → HCID 71270855, Verbindung

HRID 510449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510449
[CH3:1][C:2]1[C:19]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[C:5]2[N:6]=[C:7]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:8]=[C:9]([C:10]([NH2:12])=O)[N:4]2[N:3]=1.S(Cl)(Cl)=O.O>CN(C)C=O>[CH3:1][C:2]1[C:19]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[C:5]2[N:6]=[C:7]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:8]=[C:9]([C:10]#[N:12])[N:4]2[N:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24386Thionyl Chloride2×HCID 71270697HCID 71270697, Verbindung

Produkt 1

HCID 71270855HCID 71270855, VerbindungAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the solution of 2-methyl-5-(4-morpholinyl)-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine-7-carboxamide (0.2 g, 0.498 mmol) in N,N-Dimethylformamide (DMF) (4 mL) was added thionyl chloride (0.055 mL, 0.747 mmol). The reaction was stirred at rt for 1 h. Additional thionyl chloride (0.055 mL, 0.747 mmol) was added in. The reaction was stirred at rt for 1 h. Water was added in. The solid precipitated. Filtration gave the crude product. The crude was purified on silica column (20˜50% EtOAc/Hexane) to give the product (0.06 g, 31%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H) 3.58-3.72 (m, 8H) 4.34 (s, 2H) 7.30 (d, J=7.07 Hz, 1H) 7.36-7.45 (m, 1H) 7.46-7.54 (m, 2H) 7.58 (s, 1H) 7.77 (d, J=7.83 Hz, 1H) 7.83-7.95 (m, 1H) 8.40 (d, 1H); LC/MS: MS (ES+) m/e 384.2 [M+H]+.

Aufarbeitung

  1. stirringThe reaction was stirred at rt for 1 h
  2. customThe solid precipitated
  3. filtrationFiltration
  4. customgave the crude product
  5. customThe crude was purified on silica column (20˜50% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-404a47437ea0416db4e22d454ae0189d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096605B2

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