Cesium carbonate → 7-({2-[(Cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

HRID 1640178Notes

Reaction equation

HRID 1640178 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH:5]=1)([O-])=O.[OH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][CH:23]([C:27]([OH:29])=[O:28])[CH2:24]2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:13]1([C:11]([NH:10][C:6]2[CH:5]=[C:4]([O:16][C:17]3[CH:26]=[C:25]4[C:20]([CH2:21][CH2:22][CH:23]([C:27]([OH:29])=[O:28])[CH2:24]4)=[CH:19][CH:18]=3)[CH:9]=[CH:8][N:7]=2)=[O:12])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 145412687-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidHCID 58902368N-(4-nitropyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 589022317-({2-[(Cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-nitropyridin-2-yl)cyclopropanecarboxamide (2.75 g, 13.3 mmol), 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2.55 g, 13.3 mmol) and Cs2CO3.(13.0 g, 39.8 mmol) in DMF (40 mL) was heated at 80° C. for 18 h. The reaction mixture was cooled to rt and concentrated. The residue was acidified to approximately pH 3 by the addition of 1N HCl. The precipitate was filtered and washed with water then hexane and dried under vacuum to provide 7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (4.08 g, 87.2%) as a beige solid. LCMS: (FA) ES+ 353.2, ES− 351.3.

Workup

  1. concentrationconcentrated
  2. additionThe residue was acidified to approximately pH 3 by the addition of 1N HCl
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. dry with materialhexane and dried under vacuum

Sources & evidence

ORD record
ord-683ccb5dc0bc4467bd2521df7c35a1c5
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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