Ethanol → N-[4'-methyl-2-(2-morpholin-4-yl-2-oxoethyl)-4,5'-bi-1,3-thiazol-2'-yl]acetamide

HRID 1715296Notes

Reaction equation

HRID 1715296 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](OCC)=O)[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[N:21]1([C:27](=S)CC(N)=O)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)CC)C.CC[OH:42]>>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:11]1[N:12]=[C:13]([CH2:16][C:27]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:42])[S:14][CH:15]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 11989521Ethyl 2'-(acetylamino)-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxylate2×HCID 867611803-Morpholin-4-yl-3-thioxo-propionamide

Product 1

HCID 11990233N-[4'-methyl-2-(2-morpholin-4-yl-2-oxoethyl)-4,5'-bi-1,3-thiazol-2'-yl]acetamideYield 41%

Procedure

N-[5-(bromoacetyl)-4-methyl-1,3-thiazol-2-yl]acetamide, hydrobromide salt (Intermediate 1) (300 mg; 0.84 mmol; 1 eq) and 3-morpholin-4-yl-3-thioxo-propionamide (157.7 mg; 0.84 mmol; 1 eq) are dissolved in EtOH (10 ml). Triethylamine (0.29 ml; 2.09 mmol; 2.5 eq) is added. The mixture is stirred overnight at RT. Solvents are evaporated and the crude product is dissolved in EtOAc and washed with water, brine and dried over MgSO4. After filtration and evaporation of the solvents, the resulting yellow solid is dissolved in a DCM, Et2O and EtOH mixture. Concentration of this solution results in the precipitation of Compound (56) as yellow solid (126.2 mg; 41%)

Workup

  1. customSolvents are evaporated
  2. dissolutionthe crude product is dissolved in EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and evaporation of the solvents
  6. dissolutionthe resulting yellow solid is dissolved in a DCM, Et2O and EtOH mixture

Sources & evidence

ORD record
ord-dbb5672707ec4f4fa47fc72b754c00a7
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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