Stannous Chloride → 3-amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide

HRID 1943942ノート

反応式

HRID 1943942 の反応式
[F:1][C:2]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[C:18]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15]([O:16][CH3:17])=[N:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:22][C:21]1[C:2]([F:1])=[C:3]([C:18]([F:25])=[CH:19][CH:20]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:15]([O:16][CH3:17])=[N:14][NH:13][C:10]2=[N:11][CH:12]=1)=[O:5]

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 670890542,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-nitrobenzamide

生成物 1

HCID 670889003-amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide収率 84.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

2,6-Difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-nitrobenzamide (762.3 mg, 2.183 mmol) was dissolved in ethyl acetate (21.8 mL) and treated with tin (II) chloride dehydrate (2463 mg, 10.91 mmol). The reaction mixture was heated to reflux for 2 hours and then allowed to cool to ambient temperature. The reaction mixture was quenched with saturated sodium carbonate and filtered. The filtrate was washed with water (2×), sodium bicarbonate (2×), and brine (1×), dried over sodium sulfate, and concentrated to afford 3-amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (588.2 mg, 1.842 mmol, 84.4% yield) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.629-12.519 (s, 1H), 10.980-10.883 (s, 1H), 8.675-8.583 (s, 1H), 8.544-8.458 (s, 1H), 6.993-6.811 (m, 2H), 5.297-5.188 (s, 2H), 4.093-3.973 (s, 3H); MS (APCI-pos) m/z=320.3 (M+H).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe reaction mixture was quenched with saturated sodium carbonate
  4. filtrationfiltered
  5. washThe filtrate was washed with water (2×), sodium bicarbonate (2×), and brine (1×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-54760a9b103f4315bf6c76a9a67bbec3
出典データセット
uspto-grants-2013_03
特許番号
US08394795B2

反応ノート

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