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PyBOP → 3-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1501559
ノート
印刷プレビュー

反応式

HRID 1501559 の反応式
[Br:1][C:2]1[C:10]2[C:9]([C:11](O)=[O:12])=[CH:8][C:7]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[N:6][C:5]=2[N:4]([CH:27]([CH3:29])[CH3:28])[N:3]=1.[NH2:30][CH2:31][C:32]1[C:33](=[O:40])[NH:34][C:35]([CH3:39])=[CH:36][C:37]=1[CH3:38].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CS(C)=O>[Br:1][C:2]1[C:10]2[C:9]([C:11]([NH:30][CH2:31][C:32]3[C:33](=[O:40])[NH:34][C:35]([CH3:39])=[CH:36][C:37]=3[CH3:38])=[O:12])=[CH:8][C:7]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[CH:18][CH:19]=3)=[N:6][C:5]=2[N:4]([CH:27]([CH3:29])[CH3:28])[N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 682954103-bromo-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

生成物 1

HCID 682955773-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide収率 39%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 3-bromo-1-isopropyl-6-(4-(morpholinomethyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.8 g, 1.74 mmol) and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (0.531 g, 3.49 mmol) in DMSO (8 mL) and was stirred at room temperature for 15 min. Then PYBOP (1.36 g, 2.62 mmol) was added to it and stirring was continued for 12 hr. After completion of the reaction, reaction mass was poured into ice to obtain solid, which was filtered and solid was purified by silica gel column chromatography to obtain the desired compound (39% yield). LCMS: 593.20 (M+1)+; HPLC: 97.49% (@ 254 nm) (Rt; 5.338); 1H NMR (DMSO-d6, 400 MHz) δ 11.48 (bs, 1H), 8.67 (t, 1H, J=4.8 Hz), 8.18 (d, 2H, J=8.4 Hz), 7.73 (s, 1H), 7.47 (d, 2H, J=8.4 Hz), 5.87 (s, 1H), 5.33-5.30 (m, 1H), 4.40 (d, 2H, J=4.4 Hz), 3.58 (bs, 4H), 3.53 (s, 2H), 2.38 (bs, 4H), 2.26 (s, 3H), 2.11 (s, 3H), 1.52 (d, 6H, J=6.4 Hz).

後処理

  1. customAfter completion of the reaction, reaction mass
  2. additionwas poured into ice
  3. customto obtain solid, which
  4. filtrationwas filtered
  5. customsolid was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8bad6e7a43f84155907923f06dd07e9e
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09206157B2

反応ノート

読み込み中…

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