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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
Notes
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Reaction equation

HRID 1640193 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a347d4dac9864b66995f3ae988a2b587
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08110687B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes