2-Chlorobenzothiazole → (R)-N-(benzoyl)-3-methyl-N'-[(benzothiazol-2-yl)-2-cyanoacetyl]-piperazine

HRID 7599

Reaktionsgleichung

Reaktionsgleichung von HRID 7599
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]([N:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:29])[CH2:26][C:27]#[N:28])[C@H:21]([CH3:30])[CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl[C:32]1[S:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=1>C1COCC1>[C:11]([N:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:29])[CH:26]([C:32]2[S:33][C:34]3[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=3[N:36]=2)[C:27]#[N:28])[C@H:21]([CH3:30])[CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 119872-ChlorobenzothiazoleHCID 2724254Sodium bis(trimethylsilyl)amideHCID 58630501(R)-N-benzoyl-3-methyl-N'-(2-cyano-acetyl)piperazine

Produkt 1

HCID 58680163(R)-N-(benzoyl)-3-methyl-N'-[(benzothiazol-2-yl)-2-cyanoacetyl]-piperazineAusbeute 6,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaHMDS (1.48 ml, 1M in THF) was added into a solution of (R)-N-benzoyl-3-methyl-N′-(2-cyano-acetyl)piperazine (190 mg) and 2-chlorobenzothiazole (100 mg) in THF (10 ml). After the reaction was stirred for 10 hours, 4 ml of solution was separated and quenched with MeOH. After solvents were removed under vaccum, the residue was purified using Shimadzu automated preparative HPLC System to give (R)-N-(benzoyl)-3-methyl-N′-[(benzothiazol-2-yl)-2-cyanoacetyl]-piperazine (15.4 mg).

Aufarbeitung

  1. custom4 ml of solution was separated
  2. customquenched with MeOH
  3. customAfter solvents were removed under vaccum
  4. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-a40547b8595849ebabaf584db239ee95
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087610B2

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