1,2-Dichloroethane → 2-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide

HRID 229447Notes

Reaction equation

HRID 229447 reaction equation
[Na+].[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[CH:16]=[C:15]([C:17]([O-:19])=O)[CH:14]=[CH:13][N:12]3[CH:20]=2)[CH:6]=[CH:7][CH:8]=1.C(Cl)CCl.C1[CH:26]=[CH:27][C:28]2N(O)N=[N:31][C:29]=2C=1.[O:35]1CCC[CH2:37][CH:36]1CN.C(N(CC)CC)C>CN(C=O)C>[O:35]1[CH2:26][CH2:27][CH:28]([CH2:29][NH:31][C:17]([C:15]2[CH:14]=[CH:13][N:12]3[CH:20]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=4)[N:10]=[C:11]3[CH:16]=2)=[O:19])[CH2:37][CH2:36]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 97924(Tetrahydro-2H-pyran-2-ylmethyl)amineHCID 688408032-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt

Product 1

HCID 250051882-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amideYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt (141 mg, 0.481 mmol) in DMF (2 mL) were added EDC (3 eq, 1.44 mmol, 277 mg) and HOBt (3 eq, 1.44 mmol, 195 mg). The mixture was stirred at room temperature for 15 minutes then tetrahydropyran-methylamine (1.5 eq, 0.72 mmol, 83 mg) and triethyl amine (3 eq, 1.44 mmol, 0.21 mL) were added. The reaction mixture was stirred at room temperature for 3 hours then quenched by the addition of water. The product was extracted three times with ethyl acetate and the crude product was purified by column chromatography to afford 2-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide in 65% yield. 1H NMR (DMSO-d6) δ 8.69 (1H), 8.61 (2H), 8.16 (1H), 8.11 (1H), 7.98 (1H), 7.51 (1H), 7.41 (1H), 7.38 (1H), 3.92 (2H), 3.18 (2H), 3.11 (2H), 1.95 (1H), 1.31 (2H), 1.12 (2H); m/z (M+H)=370.3

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. customthen quenched by the addition of water
  3. extractionThe product was extracted three times with ethyl acetate
  4. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-9e4cfd50547d49f7a4f5cf1e86e6802c
Source dataset
uspto-grants-2009_07
Patent number
US07563797B2

Reaction notes

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