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Cesium carbonate → Tert-butyl [7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

HRID 1640193
ノート
印刷プレビュー

反応式

HRID 1640193 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9]2)=[CH:4][CH:3]=1.[N+]([C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30]([CH:32]2[CH2:34][CH2:33]2)=[O:31])[CH:24]=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:32]1([C:30]([NH:29][C:25]2[CH:24]=[C:23]([O:1][C:2]3[CH:11]=[C:10]4[C:5]([CH2:6][CH2:7][CH:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:9]4)=[CH:4][CH:3]=3)[CH:28]=[CH:27][N:26]=2)=[O:31])[CH2:33][CH2:34]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

5

反応物 3

HCID 10796Cesium carbonateHCID 22182058Tert-butyl (7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)carbamateHCID 58902368N-(4-nitropyridin-2-yl)cyclopropanecarboxamide

生成物 1

HCID 58902285Tert-butyl [7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
65 °C

実験手順

A mixture of tert-butyl (7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate (2.07 g, 0.00707 mol), N-(4-nitropyridin-2-yl)cyclopropanecarboxamide (1.46 g, 0.00707 mol) and cesium carbonate (6.92 g, 0.0212 mol) in DMF was heated with stirring at 65° C. overnight. The reaction mixture was extracted with EtOAc. The organic solution was washed with water and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to tert-butyl [7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate. 1H NMR (CDCl3, 300 MHz) δ: 9.18 (s, 1H); 8.02 (d, 1H); 7.82 (d, 1H); 7.32 (dd, 1H); 7.11 (d, 1H); 6.90 (d, 1H); 6.78 (s, 1H); 6.58 (dd, 1H); 4.60 (s, 1H); 4.1 (m, 1H); 3.96 (s, 1H); 3.10 (d, 1H); 2.86 (m, 2H); 2.61 (dd, 1H); 2.08 (m, 1H); 2.04 (m, 1H); 1.75 (m, 1H); 1.60 (m, 1H); 1.45 (s, 9H); 1.25 (m, 1H); 1.07 (m, 2H); 0.87 (m, 2H). LCMS ES+ 424.4; ES− 422.5.

後処理

  1. temperaturewas heated
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography to tert-butyl [7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

出典と根拠

ORDレコード
ord-a347d4dac9864b66995f3ae988a2b587
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110687B2

反応ノート

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