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

반응식

[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

참가 물질

반응물 4

HCID 702Ethanol

HCID 8471Triethylamine

HCID 11989521Ethyl 2'-(acetylamino)-4'-methyl-4,5'-bi-1,3-thiazole-2-carboxylate2회

HCID 867611803-Morpholin-4-yl-3-thioxo-propionamide

생성물 1

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

실험 절차

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%)