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Ammonia → HCID 16752727, Verbindung

HRID 2194995
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2194995
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:12]=3[C:11]=2[N:10]=1.[CH3:26][NH:27][CH2:28][C:29]#[CH:30].C(N(C(C)C)CC)(C)C.O=O.N>O1CCCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:30]#[C:29][CH2:28][NH:27][CH3:26])=[CH:4][C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:12]=3[C:11]=2[N:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 5

HCID 222AmmoniaHCID 977OxygenHCID 81531DiisopropylethylamineHCID 96160N-methylpropyn-2-ylamineHCID 59254920HCID 59254920, Verbindung

Produkt 1

HCID 16752727HCID 16752727, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 13169693Triphenylphosphine palladium dichlorideKatalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1.0 g (2.1 mmol) N-[8-(2-chloro-5-iod-phenyl)-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl]-acetamide are placed in 50 mL tetrahydrofuran under an argon atmosphere and combined with 0.6 ml (9 mmol) N-methylpropargylamine and 1 mL (6 mmol) diisopropylethylamine. The mixture is kept free from oxygen and 29 mg (0.04 mmol) triphenylphosphine palladium(II)-chloride and 8 mg (0.04 mmol) copper(I)-iodide are added. The mixture is stirred for 5 hours at 80° C. After cooling to ambient temperature the reaction mixture is combined with water and 10% ammonia solution and extracted with dichloromethane. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography, the product obtained is triturated with diethyl ether and suction filtered.

Aufarbeitung

  1. additionare added
  2. temperatureAfter cooling to ambient temperature the reaction mixture
  3. extractionextracted with dichloromethane
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography
  7. customthe product obtained
  8. customis triturated with diethyl ether and suction
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-9a5684583c124713b8f3efa1dcca2a5f
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08334378B2

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