Cyclohexanepentanoic acid → HCID 178520569, compound

HRID 1071993Notes

Reaction equation

HRID 1071993 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:14]1[C:22]2[CH2:21][CH2:20][NH:19][CH2:18][C:17]=2[N:16]=[CH:15]1>C(Cl)Cl>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:19]2[CH2:20][CH2:21][C:22]3[NH:14][CH:15]=[N:16][C:17]=3[CH2:18]2)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 94769Cyclohexanepentanoic acidHCID 178420865HCID 178420865, compound

Product 1

HCID 178520569HCID 178520569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 5-cyclohexylpentanoic acid (0.94 g, 5.10 mmol) in DCM (4 mL) carbonyldiimidazole (0.83 g, 5.12 mmol) was added. The resulting mixture was stirred at room temperature for 16 h and then added to a solution of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine (5.10 mmol) in DCM (4 mL). After 2.5 h DCM (50 mL) was added and the mixture was washed with water (3×15 mL). The organic layer was then dried (MgSO4) and concentrated. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol 9:1) whereby 0.35 g (24%) of the title amide was obtained as an oil.

Workup

  1. washthe mixture was washed with water (3×15 mL)
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol 9:1) whereby 0.35 g (24%) of the title amide
  5. customwas obtained as an oil

Sources & evidence

ORD record
ord-ff05c2dcbb3948a69c1c196d26ff8510
Source dataset
uspto-grants-2005_06
Patent number
US06908926B1

Reaction notes

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