Cyclobutanecarbonyl chloride → N-((5-Oxo-4,5-dihydro-1,2,4-triazin-6-yl)methyl)cyclobutanecarboxamide

HRID 17978

反応式

HRID 17978 の反応式
[NH2:1][CH2:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[N:7][N:8]=1.CCN(C(C)C)C(C)C.[CH:19]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][CH2:20]1>CN(C=O)C.N1C=CC=CC=1>[O:9]=[C:4]1[C:3]([CH2:2][NH:1][C:23]([CH:19]2[CH2:22][CH2:21][CH2:20]2)=[O:24])=[N:8][N:7]=[CH:6][NH:5]1

参加物

6

反応物 3

HCID 78705Cyclobutanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 1357424956-(Aminomethyl)-1,2,4-triazin-5(4H)-one

生成物 1

HCID 135993273N-((5-Oxo-4,5-dihydro-1,2,4-triazin-6-yl)methyl)cyclobutanecarboxamide

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-aminomethyl-4H-[1,2,4]triazin-5-one (500 mg, 3.96 mmol) and N,N′-diisopropylethylamine (DIEA) (0.829 mL, 4.76 mmol) in anhydrous N,N′-dimethylforamide (DMF) (20 mL) and anhydrous pyridine (2 mL) was dropwise charged with cyclobutanecarbonyl chloride (0.451 mL, 3.96 mmol) at 0° C. then warmed to rt and stirred for an additional 1.5 h. The reaction mixture was quenched with H2O (2 mL), concentrated in vacuo, and purified by chromatography on silica gel [eluting with 5% MeOH in CH2Cl2 (200 mL)→10% MeOH in CH2Cl2 (800 mL)], affording the title compound; 1H NMR (DMSO-d6, 400 MHz) δ 1.7-1.82 (m, 1H), 1.70-1.92 (m, 1H); 1.97-2.07 (m, 2H); 2.07-2.19 (m, 2H); 3.55-3.67 (m, 1H); 4.19 (d, 2H); 7.97 (brt, J=5.6 Hz, 1H); 8.67 (s, 1H); MS (ES+): m/z 209.25 (100) [MH+], HPLC: tR=1.56 min (MicromassZQ, polar—5 min).

後処理

  1. customThe reaction mixture was quenched with H2O (2 mL)
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography on silica gel [eluting with 5% MeOH in CH2Cl2 (200 mL)→10% MeOH in CH2Cl2 (800 mL)]

出典と根拠

ORDレコード
ord-61bbb432c7114efdb6b8e54b77be6d9a
出典データセット
uspto-grants-2010_06
特許番号
US07741324B2

関連ノート

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