Imidazole → N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-3-(1H-imidazol-1-yl)propanamide hydrochloride

HRID 916356Notes

Reaction equation

HRID 916356 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([NH:6][CH:7]1[CH2:13][CH:12]2[N:14]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]#[N:26])=[CH:17][CH:16]=3)[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)=[O:5].[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.[I-].[Na+].ClCCl>C(OCC)(=O)C>[ClH:1].[C:25]([C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([N:14]2[CH:12]3[CH2:11][CH2:10][CH:9]2[CH2:8][CH:7]([NH:6][C:4](=[O:5])[CH2:3][CH2:2][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[CH2:13]3)=[CH:16][CH:17]=1)#[N:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 6344DichloromethaneHCID 692265953-Chloro-N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]propanamide

Product 1

HCID 69225903N-[8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-3-(1H-imidazol-1-yl)propanamide hydrochlorideYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

165RL50 (61 mg, 0.17 mmol), imidazole (53 mg, 0.83 mmol), sodium iodide (10 mg, 0.07 mmol) and dichloromethane (6 mL) were shaken in a vial at 80° C. for 2 days. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with water (2×10 mL). The organic solution was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography using a stepwise gradient of 10-100% methanol in ethyl acetate to give the title compound (32 mg, 47%).

Workup

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d060973cdebd4e1e9564d2cf047e6eff
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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