Carbonate Ion → 8-(cyclohexylmethoxy)-N-cyclopropyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 64478

Reaction equation

HRID 64478 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([OH:21])=O)=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:22]1([NH2:25])[CH2:24][CH2:23]1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.N=C=N.C([NH+](CC)CC)C.C(=O)([O-])[O-].[N-]=C=O>CN(C=O)C>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:25][CH:22]4[CH2:24][CH2:23]4)=[O:21])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

10

Reactant 8

HCID 19660Carbonate IonHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 160435CarbodiimideHCID 1385867TriethylammoniumHCID 711084908-(Cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 867135068-(cyclohexylmethoxy)-N-cyclopropyl-2-methylimidazo[1,2-a]pyridine-3-carboxamideYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 8.7 mg of 8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid, 5.1 mg of cyclopropylamine, 4.1 mg of 1-hydroxybenzotriazole, 1 ml of DMF, and 28 μl of diisopropylethylamine was added 50 mg of polystyrene N-cyclohexylcarbodiimide-N′-propyloxymethyl (PS-Carbodiimide manufactured by Biotage), followed by stirring at room temperature for 16 hours. Subsequently, 1 ml of DMF, 50 mg of macroporious triethylammonium methylpolystyrene carbonate (MP-Carbonate manufactured by Biotage) and 50 mg of polystyrene methyl isocyanate (PS-Isocyanate manufactured by Biotage), followed by stirring at room temperature for 3 hours. The resin of the reaction mixture was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by preparative HPLC (high performance liquid chromatography) to obtain 8.7 mg of 8-(cyclohexylmethoxy)-N-cyclopropyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. customThe resin of the reaction mixture was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by preparative HPLC (high performance liquid chromatography)

Sources & evidence

ORD record
ord-8f5c2ad1bc3b47ae92615699a1d65b0b
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Linked notes

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