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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
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HRID 1640193 반응식
[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
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5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

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온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a347d4dac9864b66995f3ae988a2b587
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08110687B2

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