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

HRID 7599
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HRID 7599 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

HCID 58680163(R)-N-(benzoyl)-3-methyl-N'-[(benzothiazol-2-yl)-2-cyanoacetyl]-piperazine수율 6.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a40547b8595849ebabaf584db239ee95
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087610B2

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