Cyanamide → [4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanone

HRID 353736Notes

Reaction equation

HRID 353736 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[N:17]#[C:18][NH2:19].CC(C)([O-])C.[K+].Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([N+:37]([O-:39])=[O:38])[CH:31]=1)=[O:29]>C(#N)C.O>[NH2:17][C:18]1[N:19]=[C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3)=[CH:8][CH:9]=2)[S:3][C:27]=1[C:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([N+:37]([O-:39])=[O:38])[CH:31]=1)=[O:29]

Participants

7

Reactant 4

HCID 9864CyanamideHCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-oneHCID 137183971-(4-Isothiocyanatophenyl)-4-methylpiperazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 10162409[4-Amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanoneYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 1.0 g, 4.3 mmol) and cyanamide (0.2 g, 4.8 mmol) in acetonitrile (43 mL), a solution of potassium tert-butoxide (43 mL, 0.1 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(4-chloro-3-nitro-phenyl)ethanone (1.2 g, 4.3 mmol) (Maybridge Chemical Company Ltd.) was added. The reaction mixture was stirred for 4h and then poured into 50 mL of water. The product was collected by filtration, washed with water and diethyl ether. The yellow powder was dried in vacuo to provide 0.9 g (45% yield) of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanone.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with water and diethyl ether
  3. customThe yellow powder was dried in vacuo

Sources & evidence

ORD record
ord-55ef5019a79e498c98eb43d270a538f6
Source dataset
uspto-grants-2004_06
Patent number
US06756374B2

Reaction notes

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