Triethylamine → HCID 46186019, compound

HRID 1430137Notes

Reaction equation

HRID 1430137 reaction equation
[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30311302,2-DimethylpropanethioamideHCID 199742791-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-bromoethan-1-one

Product 1

HCID 46186019HCID 46186019, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f1c457f722a44acb5393ca80185f3f0
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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