Imidazole → HCID 71547904, compound

HRID 1497442Notes

Reaction equation

HRID 1497442 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:13]([C:16]1[N:21]=[CH:20][C:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:14][CH3:15]>CN(C=O)C.O>[N:1]1([CH:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:14][CH3:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 86680615HCID 86680615, compound

Product 1

HCID 71547904HCID 71547904, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of imidazole (0.077 g, 1.12 mmol), in DMF (15 mL) was added potassium carbonate (0.26 g, 1.87 mmol) and 4-(6-(1-bromopropyl)pyridin-3-yl)benzamide under nitrogen and the solution was heated to 55-60° C. for 6 h. The contents were cooled to rt, diluted with water (100 mL), extracted with ethyl acetate (2×100 mL), the layers separated, the organic layer washed with brine solution (2×30 mL), the organic layer dried over sodium sulphate and distilled off to get the crude product. The product was purified by preparative TLC (2000; 5% methanol in ethyl acetate) to give 4-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)benzamide (15 mg, 13% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.92 (s, 1H), 8.13 (d, 1H), 8.11 (s, 1H), 7.97 (d, 2H), 7.80 (t, 3H), 7.40 (d, 2H), 7.31 (s, 1H), 6.89 (s, 1H), 5.38 (q, 1H), 2.27 (m, 2H), 0.82 (t, 3H); LC-MS m/z calcd for [M+H]+ 307.37. found 307.3.

Workup

  1. temperatureThe contents were cooled to rt
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. customthe layers separated
  4. washthe organic layer washed with brine solution (2×30 mL)
  5. dry with materialthe organic layer dried over sodium sulphate
  6. distillationdistilled off
  7. customto get the crude product
  8. customThe product was purified by preparative TLC (2000; 5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-1630344de276412a80e09f6a72139e40
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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