Cyanamide → HCID 21958922, 화합물

HRID 10813노트

반응식

HRID 10813 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 21958922HCID 21958922, 화합물수율 50%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eeb6facdc8e0446389e7e7456b4ead4b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094896B2

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