Water → HCID 86710017, compound

HRID 1468257Notes

Reaction equation

HRID 1468257 reaction equation
[CH:1]1([CH2:7][C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17](=[O:23])[N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:16][C:11]3=[N:10][C:9]=2[C:24]([OH:26])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.Cl.[CH3:51][NH:52][O:53][CH3:54].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH:1]1([CH2:7][C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17](=[O:23])[N:18]([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:16][C:11]3=[N:10][C:9]=2[C:24]([N:52]([O:53][CH3:54])[CH3:51])=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 7

HCID 962WaterHCID 1049PyridineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86710018HCID 86710018, compound

Product 1

HCID 86710017HCID 86710017, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Cyclohexylmethyl-7-(N,N-diethylcarbamoyl)imidazo[1,2-a]pyridine-2-carboxylic acid (181 mg, 0.506 mmol) obtained in step 1 of Example 2 was dissolved in DMF (1.8 mL), and the solution was stirred at room temperature for 2 hours after adding EDC.HCl (146 mg, 0.760 mmol), HOBt.H2O (116 mg, 0.760 mmol), N,O-dimethylhydroxylamine hydrochloride (74.0 mg, 0.760 mmol), and pyridine (0.0610 mL, 0.760 mmol). Under ice-cooled condition, a saturated sodium hydrogen carbonate aqueous solution was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5) to give 3-cyclohexylmethyl-7-(N,N-diethylcarbamoyl)-N-methoxy-N-methylimidazo[1,2-a]pyridine-2-carboxamide (200 mg, yield 99%).

Workup

  1. temperatureUnder ice-cooled condition
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5)

Sources & evidence

ORD record
ord-967b1539e5904471baf962a31c5f306c
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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