Triethylamine → Isoquinoline,6-[[1-(2-pyrimidinyl)-4-piperidinyl]oxy]-,hydrochloride

HRID 1887089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887089
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][N:28]=1>N1C=CC=CC=1>[ClH:26].[N:28]1[CH:27]=[CH:32][CH:31]=[N:30][C:29]=1[N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6428344-ChloropyrimidineHCID 674289666-(Piperidin-4-yloxy)-isoquinoline hydrochloride

Produkt 1

HCID 67430385Isoquinoline,6-[[1-(2-pyrimidinyl)-4-piperidinyl]oxy]-,hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

150 mg of 6-(Piperidine-4-yloxy)-isoquinoline hydrochloride (124) are dissolved in 10 mL of dry pyridine. 177 mg of triethylamine and 69 mg of 4-chloropyrimidine are added and the solution is stirred at 65° C. for 6 hours. The reaction mixture is poured on brine and extracted three times with ethyl acetate. The combined organic layers are dried over magnesium sulfate, evaporated to dryness and the crude product is purified by preparative HPLC. The product is converted into the corresponding HCl salt by taking up the product in 20 mL of 1 N hydrochloric acid followed by lyophilization. Yield: 47 mg. Rt=1.05 min (Method #2). Detected mass: 307.1 (M+H+).

Aufarbeitung

  1. additionThe reaction mixture is poured on brine
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. customevaporated to dryness
  5. customthe crude product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8357e05c230b4d849dc65ac696a0de98
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501736B2

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