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Diisopropylethylamine → 5-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 1472873
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1472873
Cl.[NH2:2]O.C(N(C(C)C)CC)(C)C.[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[N:28]=[C:27]([NH:29][C:30]([NH:32]C(OCC)=O)=S)[CH:26]=[C:25](OC)[CH:24]=3)=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1.[CH2:40]([OH:42])C.CO>>[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[N:28]4[N:2]=[C:30]([NH2:32])[N:29]=[C:27]4[CH:26]=[CH:25][C:24]=3[O:42][CH3:40])=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1
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Komponenten

5

Edukt 4

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 18681192Ethanol, mixt. with methanolHCID 866479261-[6-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-4-methoxy-pyridin-2-yl]-3-carboethoxy-thiourea

Produkt 1

HCID 595896845-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Versuchsvorschrift

To a mixture ethanol/methanol (5 mL/5 mL), hydroxylamine hydrochloride (0.47 g, 6.8 mmol) and diisopropylethylamine (0.71 mL, 4.08 mmol) were added successively. The mixture was stirred for 1 hour and 1-[6-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-4-methoxy-pyridin-2-yl]-3-carboethoxy-thiourea was added portionwise. The mixture was refluxed for 3 hours and then allowed to cool to room temperature. The solvent was removed under reduced pressure, and the resulting solid collected by filtration and washed with water followed by methanol. The solid was used without further purification (0.33 g, 80%). LCMS Method: 2: RT: 2.57 min, MI: 299 [M+1].

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. filtrationthe resulting solid collected by filtration
  4. washwashed with water
  5. customThe solid was used without further purification (0.33 g, 80%)

Quellen und Nachweise

ORD-Eintrag
ord-eb89dee287214f9fb31a1bfebec869a7
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012633B2

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