4-(Aminomethyl)-1-(1-phenylethyl)piperidin-4-amine → HCID 178435989, Verbindung

HRID 2365515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365515
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](=[NH:16])SC)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[NH2:17][CH2:18][C:19]1(N)[CH2:24][CH2:23][N:22]([CH:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[CH2:21][CH2:20]1>CC(O)C.CO>[C:27]1([CH:25]([N:22]2[CH2:23][CH2:24][C:19]3([NH:16]/[C:13](=[N:12]/[C:10]([C:3]4[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=4)=[O:11])/[NH:17][CH2:18]3)[CH2:20][CH2:21]2)[CH3:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

5

Edukt 2

HCID 670868704-(Aminomethyl)-1-(1-phenylethyl)piperidin-4-amineHCID 1404443183,5-Diamino-6-chloro-N-[(methylsulfanyl)methanimidoyl]pyrazine-2-carboxamide2×

Produkt 1

HCID 178435989HCID 178435989, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A)(1.7 g, 4.54 mmol) and 4-aminomethyl-1-(1-phenyl-ethyl)-piperidin-4-ylamine (Intermediate BM) (1.6 g, 4.59 mmol) in propan-2-ol (50 ml) is stirred at 80° C. for 16 hours. The reaction mixture is concentrated in vacuo and purified by column chromatography (basic alumina, 0-2% MeOH in DCM) to obtain pale yellow solid. The compound obtained is further dissolved in MeOH and precipitated by adding diethyl ether. The supernatant solvent mixture is decanted and the product is washed again with diethyl ether and dried under vacuum to afford the title compound as off-white solid; [M+H]+ 429

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompurified by column chromatography (basic alumina, 0-2% MeOH in DCM)
  3. customto obtain pale yellow solid
  4. customThe compound obtained
  5. customprecipitated
  6. additionby adding diethyl ether
  7. customThe supernatant solvent mixture is decanted
  8. washthe product is washed again with diethyl ether
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-88507c851e344c69a6a34634dc6c6faf
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697687B2

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