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Water → N4-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-N6-methyl-1H-pyrazolo[3,4-b]pyridine-4,6-dicarboxamide

HRID 1854058
ノート
印刷プレビュー

反応式

HRID 1854058 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:19]=[C:18]([C:20](O)=[O:21])[N:17]=[C:16]2[N:23]([CH:26]([CH3:28])[CH3:27])[N:24]=[CH:25][C:15]=12)=[O:13].CN.C1C[N:34]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:33]C1.F[P-](F)(F)(F)(F)F.O>CS(C)=O.CO.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:25]=[N:24][N:23]([CH:26]([CH3:27])[CH3:28])[C:16]=2[N:17]=[C:18]([C:20]([NH:34][CH3:33])=[O:21])[CH:19]=1)=[O:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 6329MethylamineHCID 2724699PyBOPHCID 683512284-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylic acid

生成物 1

HCID 68295268N4-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-N6-methyl-1H-pyrazolo[3,4-b]pyridine-4,6-dicarboxamide収率 8%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

4-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylic acid (1 equiv.) was dissolved in DMSO and methylamine (2 equiv.) was added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (1.5 equiv.) was added to it and stirring was continued overnight. After completion of the reaction, water was added to it and extraction was carried out using 20% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography/prep. HPLC to give the desired compound (8% yield). LCMS: 397.15 (M+1)+; HPLC: 93.04% (@ 254 nm) (Rt; 5.597); 1H NMR (DMSO-d6, 400 MHz) δ 11.53 (s, 1H), 9.04 (t, 1H, J=4.4 Hz), 8.95 (d, 1H, J=4.8 Hz), 8.43 (s, 1H), 8.17 (s, 1H), 5.88 (s, 1H), 5.49-5.43 (m, 1H), 4.36 (d, 2H, J=4.8 Hz), 2.88 (d, 3H, J=4.4 Hz), 2.21 (s, 3H), 2.12 (s, 3H), 1.52 (d, 6H, J=6.8 Hz).

後処理

  1. additionwas added to it
  2. additionwas added to it and extraction
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude material which
  8. customwas purified by column chromatography/prep

出典と根拠

ORDレコード
ord-4f5c25de52fb49cb9d3b2ad710d9c341
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962620B2

反応ノート

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