Cesium carbonate → N-(4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

HRID 1051418Notes

Reaction equation

HRID 1051418 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][CH2:8][CH3:9])[NH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC.Br[C:27]1[N:28]=[CH:29][S:30][C:31]=1[NH:32][C:33](=[O:35])[CH3:34]>CN(C=O)C.[Cu]I>[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][CH2:8][CH3:9])[N:5]([C:27]2[N:28]=[CH:29][S:30][C:31]=2[NH:32][C:33](=[O:35])[CH3:34])[CH:6]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 83680500N-(4-bromo-1,3-thiazol-5-yl)acetamideHCID 178440092HCID 178440092, compound

Product 1

HCID 86715554N-(4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A flask was charged with 4-methyl-2-propyl-1H-imidazole from example 1.6 (140 mg, 1.13 mmol), Cs2CO3 (1.10 g, 3.39 mmol) and copper (I) iodide (108 mg, 0.56 mmol). A solution of (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (80 mg, 0.56 mmol,) and N-(4-bromothiazol-5-yl)acetamide from example 1.5 (250 mg, 1.13 mmol) in DMF (30 mL) was added under N2. The mixture was heated at 90° C. for overnight. It was concentrated and directly used for the next step without further purification.

Workup

  1. concentrationIt was concentrated
  2. customdirectly used for the next step without further purification

Sources & evidence

ORD record
ord-f27bd79f2fd74948aff96873b9580126
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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