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Sodium Bicarbonate → N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide

HRID 2388923
ノート
印刷プレビュー

反応式

HRID 2388923 の反応式
[CH3:1][N:2]([CH3:42])[C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[O:26])[CH:20]=4)[CH:17]=3)[N:12](COCC[Si](C)(C)C)[N:11]=2)[CH:5]=1.C(=O)(O)[O-].[Na+]>Cl(O)(=O)(=O)=O.C(O)(=O)C>[CH3:1][N:2]([CH3:42])[C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([N:27]5[CH2:28][CH2:29][O:30][CH2:31][CH2:32]5)=[O:26])[CH:20]=4)[CH:17]=3)[NH:12][N:11]=2)[CH:5]=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 2

HCID 516892Sodium BicarbonateHCID 59836180N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide

生成物 1

HCID 178484436N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide収率 18%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 24247
Perchloric Acid
溶媒

実験手順

A solution of N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide in 5% of perchloric acid in acetic acid (1 mL) was stirred for 1 h at room temperature. Saturated sodium bicarbonate solution was then added to the solution slowly until pH 8 and the mixture was stirred for 24 hours at room temperature. Ethyl acetate was then used for extraction and the organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. Mass triggered reverse phase HPLC purification afforded N,N-dimethyl-3-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)benzamide (7.4 mg, 18% yield over two steps) as light yellow solids. 1H NMR (500 MHz, CDCl3) δ 2.99 (s, 3H), 3.10 (s, 3H), 3.46 (br, 2H), 3.61 (br, 2H), 3.76 (br, 4H), 7.40 (d, J=7.0 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.52 (m, 2H), 7.64 (d, J=7.5 Hz, 1H), 7.68 (s, 1H), 7.98 (m, 2H), 8.62 (s, 1H), 8.85 (br, 1H). MS: m/z 456.1 (M+H+).

後処理

  1. extractionEthyl acetate was then used for extraction
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customphase HPLC purification

出典と根拠

ORDレコード
ord-ca64316658974a8d916c4a8c08a54638
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08268994B2

反応ノート

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