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Dimethylformamide → N-(4-fluorophenyl)-N-(6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-yl)cyclopropane-1,1-dicarboxamide

HRID 2241209
ノート
印刷プレビュー

反応式

HRID 2241209 の反応式
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[N:23]=[CH:22][C:21](N)=[CH:20][CH:19]=4)=[C:11]3[C:10]([CH3:25])=[N:9]2)=[CH:5][CH:4]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]([C:38]2([C:41](F)=[O:42])[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1.C[N:45](C=O)C.CCN(C(C)C)C(C)C>O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]([C:21]2[CH:22]=[N:23][C:18]([O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]4[N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=5)[N:9]=[C:10]([CH3:25])[C:11]=34)=[CH:19][CH:20]=2)[C:36]([C:38]2([C:41]([NH2:45])=[O:42])[CH2:40][CH2:39]2)=[O:37])=[CH:31][CH:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 685181536-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-amineHCID 866146491-((4-Fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride

生成物 1

HCID 68512422N-(4-fluorophenyl)-N-(6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-yl)cyclopropane-1,1-dicarboxamide
収率 59%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A 100 mL round-bottomed flask was charged with 6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-amine (0.500 g, 1.38 mmol), 1-((4-fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride (0.545 g, 2.42 mmol; prepared as in Example 6, Step A), and DMF (10 mL). DIEA (0.723 mL, 4.15 mmol) was added under nitrogen and the reaction mixture was heated at 50° C. for 18 hours. The reaction mixture was cooled to room temperature, diluted with water (100 mL), and extracted with EtOAc (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to provide the crude product (1.55 g, 59%). LRMS (esi+) 567 (M+H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f55968349cd04124a965ba67263ed607
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07723330B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート