Sodium Iodide → HCID 58387995, compound

HRID 2080239Notes

Reaction equation

HRID 2080239 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:8].[OH-].[Na+].[CH:24]1([CH2:27]Br)[CH2:26][CH2:25]1.[I-].[Na+]>C(#N)C.O.FC(F)(F)C(O)=O.O1CCCC1>[CH:24]1([CH2:27][O:1][C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[CH2:5][NH:6][C:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)=[O:8])[CH2:26][CH2:25]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 81503BromomethylcyclopropaneHCID 58875319HCID 58875319, compound

Product 1

HCID 58387995HCID 58387995, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolvent2×HCID 8028TetrahydrofuranSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture of quinoline-6-carboxylic acid 3-hydroxybenzylamide described in Preparation Example E+-4 (87 mg, 0.31 mmol) and tetrahydrofuran (2 mL) was added an aqueous solution of 1N sodium hydroxide (0.31 mL, 0.31 mmol), and the solvent was evaporated in vacuo. To a mixture of a portion (5.0 mg) of the residue (93 mg) and N,N-dimethylformamide (1 mL) were added cyclopropylmethyl bromide (2.7 mg, 0.020 mmol) and catalytic amount of sodium iodide at room temperature, followed by stirring for 3 hours at the same temperature. The reaction solution was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (1.50 mg, 0.0034 mmol, 20%) was obtained.

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionTo a mixture of a portion (5.0 mg) of the residue (93 mg) and N,N-dimethylformamide (1 mL)

Sources & evidence

ORD record
ord-1ffb559164094a9d87aab4c403a11b67
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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