Cyanamide → HCID 21958922、化合物

HRID 10813ノート

反応式

HRID 10813 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][CH:33]=[C:32]([S:36][CH3:37])[CH:31]=1)=[O:29]>C(#N)C.C(O)(C)(C)C.C(OCC)(=O)C>[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][CH:33]=[C:32]([S:36][CH3:37])[CH:31]=1)=[O:29]

参加物

8

反応物 4

HCID 9864CyanamideHCID 137183971-(4-Isothiocyanatophenyl)-4-methylpiperazineHCID 219589582-Bromo-1-[3-(methylsulfanyl)phenyl]ethan-1-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 21958922HCID 21958922、化合物収率 50%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 0.466 g, 2.0 mmol) and cyanamide (0.088 g, 2.1 mmol) in acetonitrile (3 mL) and t-butanol (5 ml), a solution of potassium tert-butoxide (2.0 mL, 1.0 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(3-methylsulfanyl-phenyl)ethanone (which can be prepared by the procedure of Rogers, N. H. et. al. EP 87953; 0.49 g, 2.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 15 minutes. The cooled mixture was diluted with ethyl acetate and washed in turn with saturated aqueous sodium carbonate and brine. The dried (sodium sulfate) solution was evaporated and the residue chromatographed on silica gel. Elution of the desired product with 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane provided 0.439 g (50% yield) of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](3-methylsulfanyl-phenyl)methanone. Mass spectrum (ES) MH+=440.

後処理

  1. addition0.49 g, 2.0 mmol) was added
  2. temperaturerefluxed for 15 minutes
  3. washwashed in turn with saturated aqueous sodium carbonate and brine
  4. dry with materialThe dried (sodium sulfate) solution
  5. customwas evaporated
  6. customthe residue chromatographed on silica gel
  7. washElution of the desired product
  8. customwith 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-eeb6facdc8e0446389e7e7456b4ead4b
出典データセット
uspto-grants-2006_08
特許番号
US07094896B2

反応ノート

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