Triethylamine → HCID 14338589, compound

HRID 706000Notes

Reaction equation

HRID 706000 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].[CH2:6](N(CC)CC)C.C[O:14][C:15](=O)[C:16]([CH:18](OC(=O)C)[C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=C>CCO>[CH3:6][S:4][C:3]1[NH:5][C:15](=[O:14])[C:16]([CH2:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[CH:1][N:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723704MethylthioureaHCID 67775493HCID 67775493, compound

Product 1

HCID 14338589HCID 14338589, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Methyl thiourea (0.492 g, 2.28 mmol, 1.1 eq) was dissolved in EtOH (dried over mol. sieves) (2 ml) and triethyl amine (0.633 ml, 2.2 eq) was added. Reaction mixture was heated to 70° C. and 2-(acetoxy-thiazol-2-yl-methyl)-acrylic acid methyl ester (0.5 g, 2.07 mmol, 1 eq) dissolved in EtOH (dried over mol. sieves) (2 ml), was added. It was heated at 70° C. for 8 h and then, it was cooled and filtered. Filtrate was evaporated to dryness and purified via Biotage SP1 Snap 25 g, 25 ml/min; in system MeOH/DCM 1-30% MeOH in 30 CV. Appropriate fractions were combined and evaporated to give 250 mg of brown powder.

Workup

  1. customReaction mixture
  2. additionwas added
  3. temperatureIt was heated at 70° C. for 8 h
  4. temperatureit was cooled
  5. filtrationfiltered
  6. customFiltrate was evaporated to dryness
  7. custompurified via Biotage SP1 Snap 25 g, 25 ml/min
  8. customevaporated

Sources & evidence

ORD record
ord-cc74687d2a0a4a7b99efb4685c457a1b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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