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

HRID 10798

反応式

HRID 10798 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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 4 h 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.

後処理

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

出典と根拠

ORDレコード
ord-0ed24783b19a418792f2d568d95728e8
出典データセット
uspto-grants-2006_08
特許番号
US07094896B2

関連ノート

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