Ammonium Chloride → 3-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide

HRID 2070709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070709
[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11](OC)=[O:12])[CH:7]=1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.C([Mg]Cl)(C)C.[NH4+].[Cl-]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:20]2[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[C:5](=[O:19])[N:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11]([NH:30][CH:27]2[CH2:29][CH2:28]2)=[O:12])[CH:7]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 69828CyclopropylamineHCID 866632373-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl esterHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 666864943-[5-Chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-N-cyclopropyl-4-methyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[5-chloro-3-(4-methyl-1-piperazinyl)-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester (Example 107b) in tetrahydrofuran (6 mL) under nitrogen was added cyclopropylamine (0.15 mL) followed by iso-propylmagnesium chloride (2M in tetrahydrofuran, 0.8 mL), portionwise. After 1 h, sat. aqueous NH4Cl was added and the mixture extracted into ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. Purification by preparative HPLC (Gemini column, 0.1% ammonia: acetonitrile eluent) afforded the title compound (35 mg).

Aufarbeitung

  1. extractionthe mixture extracted into ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customPurification by preparative HPLC (Gemini column, 0.1% ammonia: acetonitrile eluent)

Quellen und Nachweise

ORD-Eintrag
ord-16e210ffb108430db1f2e1d1adbe707f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299246B2

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