18-Crown-6 → HCID 117667385, Verbindung

HRID 1526236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526236
Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[CH2:33]([N:40]1[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH2:45][OH:46])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.O.O1CCOCC1>[CH2:33]([N:40]1[CH2:44][CH2:43][CH2:42][C@@H:41]1[CH2:45][O:46][C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

8

Edukt 4

HCID 2855718-Crown-6HCID 719766(R)-1-N-Benzyl-prolinolHCID 23665647Potassium tert-butoxideHCID 885697085-Chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide

Produkt 1

HCID 117667385HCID 117667385, VerbindungAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (300 mg), [(2R)-1-benzylpyrrolidin-2-yl]methanol (251 mg), 18-crown-6 (346 mg), potassium t-butoxide (147 mg), and dioxane (3 mL) was stirred at 100° C. for 5 hours. To the mixture were added water and ethyl acetate, followed by liquid separation. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate:chloroform=1:1) to obtain 5-{[(2R)-1-benzylpyrrolidin-2-yl]methoxy}-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (201 mg) as a yellow solid.

Aufarbeitung

  1. customfollowed by liquid separation
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate:chloroform=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7737effb7d70488181e35ce49d2d0d5d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085540B2

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