1-Methylpiperazine → N-(6-Bromo-1,3-benzothiazol-2-yl)-N'-[4-(4-methylpiperazino)-4-oxobutyl]urea

HRID 9164

Reaction equation

HRID 9164 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=O)=[O:11])[S:8][C:4]=2[CH:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C1COCC1>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]([N:27]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)=[O:18])=[O:11])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 21985597Ethyl 4-([(6-bromo-1,3-benzothiazol-2-yl)amino]carbonylamino)butanoate

Product 1

HCID 21985590N-(6-Bromo-1,3-benzothiazol-2-yl)-N'-[4-(4-methylpiperazino)-4-oxobutyl]ureaYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-([(6-bromo-1,3-benzothiazol-2-yl)amino]carbonylamino)butanoate (100 mg, 0.259 mmol) was heated neat at about 80° C. in N-methyl-piperazine (259 mg, 2.59 mmol) for about 8 hrs. To the crude reaction mixture was added THF (2 mL), the ppt was filtered off and washed with THF (1 mL). The product was dried in vacuo and gave 67 mg (53%) pure product.

Workup

  1. customTo the crude reaction mixture
  2. filtrationthe ppt was filtered off
  3. washwashed with THF (1 mL)
  4. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-a7c760657744469984c092df1b5dee3f
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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