Sodium Hydroxide → HCID 178502871, compound

HRID 2080240Notes

Reaction equation

HRID 2080240 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=S)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrCC1C=CC2C(=CC=CC=2)C=1.Cl.[O:42]([NH2:44])[CH3:43].[OH-].[Na+]>C(#N)C.O.FC(F)(F)C(O)=O.CN1CCCC1=O.C(#N)C>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)=[N:44][O:42][CH3:43])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 703202-BromomethylnaphthaleneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 58875330HCID 58875330, compound

Product 1

HCID 178502871HCID 178502871, compoundYield 6.4%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture of quinoline-6-carbothioic acid 4-benzyloxy-benzylamide described in Preparation Example E+-10 (57 mg, 0.15 mmol) and acetonitrile (3 mL) was added 2-(bromomethyl)naphthalene (200 mg, 0.94 mmol), which was then refluxed for 2 hours. After cooling, the solvent was evaporated in vacuo, and the residue was washed with diethyl ether three times. A mixture of a portion (29 mg) of the resulting crude product (57 mg), methoxylamine hydrochloride (2.9 mg, 0.035 mmol), an aqueous solution of 1N sodium hydroxide (0.035 mL, 0.035 mmol) and N-methylpyrrolidinone (1 mL) was stirred at room temperature for 25 minutes. The reaction solution was directly purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and ditrifluoroacetic acid salt of the title compound (1.9 mg, 0.0030 mmol, 6.4%) was obtained.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo
  4. washthe residue was washed with diethyl ether three times

Sources & evidence

ORD record
ord-59387b7ed4f144e59dc1a7079960214d
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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