Cyclohexyl bromide → Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

HRID 2370910Notes

Reaction equation

HRID 2370910 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Br[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.CC(=O)OCC.O>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7960Cyclohexyl bromideHCID 8471TriethylamineHCID 22728543Water ethylacetateHCID 178470993HCID 178470993, compound

Product 1

HCID 11544682Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionateYield 22.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 60.1 mg (0.23 mmol) of the compound from example 1g, 37.7 mg (0.23 mmol) of bromocyclohexane and 100 μl of triethylamine in 1 ml of absolute THF was treated in a microwave at 170° C. for 40 min. The reaction solution was then taken up in a little EA/water (1:1), and the phases were separated off, dried over Na2SO4, filtered and evaporated to dryness. Purification by chromatography on RP silica gel with CH3CN/water/0.1% TFA as mobile phase and freeze-drying of the combined product fractions afforded 18.0 mg of the desired compound as bistrifluoroacetate in the form of an amorphous solid.

Workup

  1. customthe phases were separated off
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customPurification by chromatography on RP silica gel with CH3CN/water/0.1% TFA as mobile phase
  6. customfreeze-drying of the combined product fractions

Sources & evidence

ORD record
ord-13de9d4c20a745ad8e4286c2483a3358
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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