Triethylamine → HCID 46186019, 화합물

HRID 1430137노트

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HRID 1430137 반응식
[NH2:1][C:2]1[S:3][C:4]([C:8](=O)[CH2:9]Br)=[C:5]([CH3:7])[N:6]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](=[S:16])[NH2:15].C(N(CC)CC)C>C(O)C>[C:13]([C:14]1[S:16][CH:9]=[C:8]([C:4]2[S:3][C:2]([NH2:1])=[N:6][C:5]=2[CH3:7])[N:15]=1)([CH3:18])([CH3:17])[CH3:12]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 30311302,2-DimethylpropanethioamideHCID 199742791-(2-Amino-4-methylthiazol-5-YL)-2-bromoethanone

생성물 1

HCID 46186019HCID 46186019, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1-(2-amino-4-methyl-thiazol-5-yl)-2-bromo-ethanone (7.0 g, prepared as described in WO 2006/125805), 2,2-dimethylpropanethioamide (2.25 g, prepared as described by Boys and Downs in Synthetic Communications 2006, 36, 295-298.), triethylamine (7.2 ml) and ethanol (173 ml) are heated at reflux for 3.5 hours. On cooling to room temperature the reaction mixture is filtered, the filtrate evaporated and then partitioned between aqueous NaHCO3 and CH2Cl2, extracting 3×CH2Cl2. The organic layers are dried and evaporated then triturated 4× with diethyl ether (50 ml), the diethyl ether layers combined and extracted with 1M HCl (100 ml). The HCl layer is then washed 3× diethyl ether, basified with aqueous NaOH and extracted 4× diethyl ether and 2×CH2Cl2. The organic layers dried over Na2SO4 and evaporated to give the title compound as a red solid. Hplc/MS (Method B) RT 1.95 minutes, M+H 253.9.

후처리

  1. temperatureare heated
  2. temperatureat reflux for 3.5 hours
  3. filtrationis filtered
  4. customthe filtrate evaporated
  5. custompartitioned between aqueous NaHCO3 and CH2Cl2
  6. extractionextracting 3×CH2Cl2
  7. customThe organic layers are dried
  8. customevaporated
  9. customthen triturated 4× with diethyl ether (50 ml)
  10. extractionextracted with 1M HCl (100 ml)
  11. washThe HCl layer is then washed 3× diethyl ether
  12. extractionextracted 4× diethyl ether and 2×CH2Cl2
  13. dry with materialThe organic layers dried over Na2SO4
  14. customevaporated

출처 및 근거

ORD 기록
ord-9f1c457f722a44acb5393ca80185f3f0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940771B2

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