Tetrahydrofuran → (R)-N-(benzoyl)-3-methyl-N'-[2-(5-methoxy-benzothiazol-2-yl)-2-imino-1-cyano-ethyl]-piperazine

HRID 7600

Reaction equation

HRID 7600 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]#[N:26])[C@H:20]([CH3:27])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:28]([C:30]1[S:31][C:32]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:33]=2[N:34]=1)#[N:29].C1C[O:44]CC1>>[C:11]([N:18]1[CH2:23][CH2:22][N:21]([CH:24]([C:25]#[N:26])[C:28]([C:30]2[S:31][C:32]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:33]=3[N:34]=2)=[NH:29])[C@H:20]([CH3:27])[CH2:19]1)(=[O:44])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 152740725-Methoxy-1,3-benzothiazole-2-carbonitrileHCID 86601950(R)-N-benzyl-3-methyl-N'-cyanomethylpiperazine

Product 1

HCID 86601949(R)-N-(benzoyl)-3-methyl-N'-[2-(5-methoxy-benzothiazol-2-yl)-2-imino-1-cyano-ethyl]-piperazine

Procedure

NaHMDS (0.77 ml, 1M in THF) was added into a solution of (R)-N-benzyl-3-methyl-N′-cyanomethylpiperazine (100 mg) and 2-cyano-5-methoxy-benzothiazole (58 mg) in THF (10 ml). The reaction was stirred for 10 hours. Then 4 ml of the reaction mixture 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′-[2-(5-methoxy-benzothiazol-2-yl)-2-imino-1-cyano-ethyl]-piperazine (1.3 mg).

Workup

  1. customThen 4 ml of the reaction mixture was separated
  2. customquenched with MeOH
  3. customAfter solvents were removed under vaccum
  4. customthe residue was purified

Sources & evidence

ORD record
ord-28046646c1654096b7755cc2c17642b7
Source dataset
uspto-grants-2006_08
Patent number
US07087610B2

Linked notes

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