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

HRID 64478

반응식

HRID 64478 반응식
[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

참가 물질

10

반응물 8

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8f5c2ad1bc3b47ae92615699a1d65b0b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447090B2

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