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

HRID 2281588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281588
[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-cf3f906a0bc246808bd74756c5481f67
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139586B2

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