Sodium Hydroxide → HCID 68595558, Verbindung

HRID 220541

Reaktionsgleichung

Reaktionsgleichung von HRID 220541
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:22]=[N:23][NH:24][CH:25]=4)[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[ClH:28].[Cl:29][CH2:30][CH2:31][NH:32][CH3:33].[Cl-].[NH4+]>C(#N)C.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[ClH:29].[ClH:28].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]4[CH:25]=[N:24][N:23]([CH2:30][CH2:31][NH:32][CH3:33])[CH:22]=4)[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 3028223Ethanamine, 2-chloro-N-methyl-, hydrochloride (1:1)HCID 59321743HCID 59321743, Verbindung

Produkt 1

HCID 68595558HCID 68595558, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dissolve 3′-(4-fluoro-phenyl)-4-(1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.450 g, 1.33 mmol) in acetonitrile (3 mL) and add solid sodium hydroxide (0.186 g, 4.65 mmol). After 30 min. add (2-chloro-ethyl)-methyl-amine hydrochloride (0.190 g, 1.46 mmol) and tetrabutylammonium bisulfate (18 mg, 0.0531 mmol) then reflux the mixture for 20 hr. Cool and filter the mixture then evaporate. Purify using silica gel chromatography, eluting with 6:94 2N ammonia in methanol:DCM to give a yellow oil. Dissolve the solid in methanol and add ammonium chloride then sonicate the mixture for 10 min. Evaporate the solution to give the title compound as a white solid (0.139 g, 23%). MS (ES): m/z=396 [M+H]+.

Aufarbeitung

  1. temperaturethen reflux the mixture for 20 hr
  2. temperatureCool
  3. filtrationfilter the mixture
  4. customthen evaporate
  5. customPurify
  6. washeluting with 6:94 2N ammonia in methanol
  7. customDCM to give a yellow oil
  8. customthen sonicate the mixture for 10 min
  9. customEvaporate the solution

Quellen und Nachweise

ORD-Eintrag
ord-9fc5132842d847008eb03b8a484a7813
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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