Nitrogen → HCID 90412434, compound

HRID 2175948Notes

Reaction equation

HRID 2175948 reaction equation
[N:1]1[NH:2][N:3]=[CH:4][CH:5]=1.N#N.Br[C:9]1[C:10]([C:16]#[N:17])=[N:11][CH:12]=[CH:13][C:14]=1[CH3:15].CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I.O>[CH3:15][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([C:16]#[N:17])[C:9]=1[N:2]1[N:3]=[CH:4][CH:5]=[N:1]1

Participants

9

Reactant 5

HCID 947NitrogenHCID 10796Cesium carbonateHCID 675161H-1,2,3-TriazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 219525743-Bromo-4-methylpyridine-2-carbonitrile

Product 1

HCID 90412434HCID 90412434, compoundYield 40.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave vial was dissolved 2H-1,2,3-triazole (0.22 mL, 3.8 mmol) and CuI (26 mg) in DMF (4 mL). The reaction mixture was degassed with N2 and 3-bromo-4-methylpicolonitrile (300 mg, 1.5 mmol) was added followed by trans-N,N′-dimethyl-1,2-cyclohexanediamine (41 μL, 0.3 mmol) and Cs2CO3 (844 mg, 2.6 mmol). The reaction mixture was heated at 120° C. for 1 h in a microwave reactor. Then H2O was added and the mixture extracted with EtOAc. The combined organic layers were dried (MgSO4). Purification via silica gel chromatography (0-50% EtOAc in heptane) gave the title compound (112 mg, 27%). MS (ESI) mass calcd. for C9H7N5, 185.2; m/z found 186 [M+H]+.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customPurification via silica gel chromatography (0-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-ad90c9539bfc4478addd5e143b8df951
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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