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5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 178483232, 화합물

HRID 2412563
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HRID 2412563 반응식
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15](=[N:18][C:19]#[N:20])SC)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:21][N:22]([CH2:24][C:25]1[O:29][C:28]([CH2:30][S:31][CH2:32][CH2:33][NH2:34])=[CH:27][CH:26]=1)[CH3:23]>C(#N)C>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]([NH:34][CH2:33][CH2:32][S:31][CH2:30][C:28]2[O:29][C:25]([CH2:24][N:22]([CH3:23])[CH3:21])=[CH:26][CH:27]=2)=[N:18][C:19]#[N:20])[N:9]=1)[C:2]([NH2:4])=[NH:3]
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참가 물질

4

반응물 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine2회HCID 178503927HCID 178503927, 화합물

생성물 1

HCID 178483232HCID 178483232, 화합물수율 19.9%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2-guanidino-4-[2-(3-cyano-2-methylisothioureido)ethylthiomethyl]thiazole (0.5 g) and 2-[5-dimethylaminomethylfuran-2-ylmethylthio]ethylamine (0.33 g) in acetonitrile (10 ml) was heated under reflux for 48 hours. A further portion of 2-[5-dimethylaminomethylfuran-2-ylmethylthio]ethylamine (0.5 g) was added and the mixture was heated under reflux for 16 hours. The mixture was evaporated to dryness and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was dried with anhydrous magnesium sulphate and evaporated. The residual gum was triturated four times with warm diethyl ether (10 ml). The residue was further purified by applying to Merck 60 F254 preparative plates and eluting with acetonitrile/ammonia (s.g. 0.880) 7:1 v/v. The product was redissolved in acetonitrile (5 ml), and the solution filtered and evaporated to give 2-guanidino-4-[2-(2-cyano-3-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]guanidino)-ethylthiomethyl]thiazole as pale brown gum (0.15 g).

후처리

  1. temperatureunder reflux for 48 hours
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours
  4. customThe mixture was evaporated to dryness
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried with anhydrous magnesium sulphate
  7. customevaporated
  8. customThe residual gum was triturated four times with warm diethyl ether (10 ml)
  9. customThe residue was further purified
  10. washeluting with acetonitrile/ammonia (s.g. 0.880) 7:1 v/v
  11. dissolutionThe product was redissolved in acetonitrile (5 ml)
  12. filtrationthe solution filtered
  13. customevaporated

출처 및 근거

ORD 기록
ord-3bfe64124a0f416da28d2f795cd14980
출처 데이터셋
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04493840

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