Hydrochloric Acid → HCID 135899325, compound

HRID 2100470Notes

Reaction equation

HRID 2100470 reaction equation
OO.C([OH:5])C.[C:6]([C:8]1[C:9]([NH:14][C:15](=O)[CH2:16][O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)#[N:7].Cl>[OH-].[Na+].O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][O:17][CH2:16][C:15]2[NH:7][C:6](=[O:5])[C:8]3[CH:13]=[CH:12][CH:11]=[N:10][C:9]=3[N:14]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 784Hydrogen PeroxideHCID 68566915HCID 68566915, compound

Product 1

HCID 135899325HCID 135899325, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydrogen peroxide (3% in H2O, 2.8 ml) and ethanol (0.6 ml) were added to a suspension of N-(3-cyano-pyridin-2-yl)-2-[2-(4-fluoro-phenyl)-ethoxy]-acetamide (900 mg, 3 mmol) in 5N NaOH (11 ml), and the mixture was heated to reflux (4 h). Upon cooling, the solution was diluted with water and acidified (HCl, pH ˜3). The precipitated title compound was filtered off, triturated with tert-butyl methyl ether, and dried. MS: m/e=300.3 [M+H+], 1H NMR (d6-DMSO): 2.89 (t, 2H), 3.77 (t, 2H), 4.45 (s, 2H), 7.04-7.12 (m, 2H), 7.28-7.33 (m, 2H), 7.54 (dd, 1H), 8.50 (d, 1H), 8.95 (d, 1H), 12.45 (bs, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux (4 h)
  3. temperatureUpon cooling
  4. customThe precipitated title compound
  5. filtrationwas filtered off
  6. customtriturated with tert-butyl methyl ether
  7. customdried

Sources & evidence

ORD record
ord-10e79497ccf54a0d9b133e085128f021
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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