1-Naphthalenecarbonyl chloride → [3-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridin-1-yl]-naphthalen-1-yl-methanone

HRID 1783786

Reaction equation

HRID 1783786 reaction equation
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].[N:18]1([CH2:24][CH2:25][C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[CH:28][N:27]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>ClCCCl>[N:18]1([CH2:24][CH2:25][C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[C:28]([C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[O:12])[N:27]=2)[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 688300163-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine

Product 1

HCID 24948211[3-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridin-1-yl]-naphthalen-1-yl-methanoneYield 48%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of naphthoylchloride (0.28 mL, 1.85 mmol) in 1,2-dichloroethane (20 mL) was added aluminum trichloride (300 mg, 2.25 mmol). The mixture was allowed to stir for 10 min. then a solution of 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine (200 mg, 0.87 mmol) in 1,2-dichloroethane (5 mL) was added. The mixture was stirred at ambient temperature for 30 min. then washed with saturated aqueous sodium bicarbonate and the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield the title compound (160 mg, 48%). 1H NMR (DMSO-d6 δ 8.56 (1H), 8.27 (1H), 8.07 (1H), 8.02 (2H), 7.76 (1H), 7.51 (4H), 7.11 (1H), 3.52 (4H), 3.18 (2H), 2.67 (2H), 2.40 (4H); m/z (M+H)=386.2.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 30 min.
  2. washthen washed with saturated aqueous sodium bicarbonate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-4a2e32fd45894d59a095857b914e8044
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Linked notes

Loading…