Nitrogen → N-(4-(4-methyl-1H-imidazol-1-yl)thiazol-5-yl)acetamide

HRID 1051431Notes

Reaction equation

HRID 1051431 reaction equation
Br[C:2]1[N:3]=[CH:4][S:5][C:6]=1[NH:7][C:8](=[O:10])[CH3:9].C([O-])([O-])=O.[Cs+].[Cs+].N#N.C[NH:20][C@@H:21]1CCC[CH2:23][C@H:22]1[NH:27][CH3:28].CC1N=CNC=1>CN(C=O)C.[Cu]I>[CH3:23][C:22]1[N:27]=[CH:28][N:20]([C:2]2[N:3]=[CH:4][S:5][C:6]=2[NH:7][C:8](=[O:10])[CH3:9])[CH:21]=1

Participants

8

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 83680500N-(4-bromo-1,3-thiazol-5-yl)acetamideHCID 178418800HCID 178418800, compound

Product 1

HCID 86715562N-(4-(4-methyl-1H-imidazol-1-yl)thiazol-5-yl)acetamideYield 20%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
90 °C

Procedure

N-(4-bromothiazol-5-yl)acetamide from example 1.5 (1 g, 4.52 mmol), CuI(869 mg, 4.52 mmol) and Cs2CO3 (2.9 g, 9.1 mmol) were combined in a flask (backfilled with N2). Trans-N,N′-dimethylcyclohexane-1,2-diamine (630 mg, 4.52 mmol) and 4-methyl-1H-imidazole (446 mg, 5.4 mmol) in DMF (10 mL) were added and the mixture was stirred at 90° C. overnight. After the mixture was cooled to room temperature, the mixture was filtered through a syringe filter (washed with DMF). The filtrate purified by prep-HPLC to give 200 mg of the pure title compound (yield: 20%).

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. filtrationthe mixture was filtered through a syringe
  3. filtrationfilter
  4. wash(washed with DMF)
  5. customThe filtrate purified by prep-HPLC

Sources & evidence

ORD record
ord-1c126b5a271f4efb965b436cc685d891
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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