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

HRID 1051427Notes

Reaction equation

HRID 1051427 reaction equation
N#N.Br[C:4]1[N:5]=[C:6]([CH3:13])[S:7][C:8]=1[NH:9][C:10](=[O:12])[CH3:11].C([O-])([O-])=O.[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC.[CH3:30][C:31]1[N:32]=[C:33]([CH2:36][CH2:37][CH3:38])[NH:34][CH:35]=1>CN(C=O)C.[Cu]I>[CH3:13][C:6]1[S:7][C:8]([NH:9][C:10](=[O:12])[CH3:11])=[C:4]([N:34]2[CH:35]=[C:31]([CH3:30])[N:32]=[C:33]2[CH2:36][CH2:37][CH3:38])[N:5]=1

Participants

8

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86715559N-(4-bromo-2-methylthiazol-5-yl)acetamideHCID 178440092HCID 178440092, compound

Product 1

HCID 86715560N-(2-methyl-4-(4-methyl-2-propyl-1H-imidazol-1-yl)thiazol-5-yl)acetamideYield 12.7%

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 (backfilled with N2) was charged with N-(4-bromo-2-methylthiazol-5-yl)acetamide (400 mg, 1.7 mmol), CuI(324 mg, 1.7 mmol) and Cs2CO3 (1.6 g, 5.1 mmol). Trans-N,N′-dimethylcyclohexane-1,2-diamine (CAS: 61798-24-1, 242 mg, 1.7 mmol) and 4-methyl-2-propyl-1H-imidazole (230 mg, 1.9 mmol) in DMF (9.0 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 was purified by prep-HPLC to give 60 mg of the pure title compound.

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 was purified by prep-HPLC

Sources & evidence

ORD record
ord-319d7e8cb8094948b0b3c496ad3cbe0c
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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