Pyridine → HCID 88593266, compound

HRID 1623823Notes

Reaction equation

HRID 1623823 reaction equation
N1C=CC=CC=1.Cl.[NH2:8][OH:9].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]2[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][C:20]=2[C:21]([NH:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[O:22])=[CH:13][CH:12]=1>CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]2[CH:33]=[CH:32][C:31](/[CH:34]=[N:8]\[OH:9])=[CH:30][C:20]=2[C:21]([NH:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[O:22])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86668208HCID 86668208, compound

Product 1

HCID 88593266HCID 88593266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridine (0.69 ml, 8.56 mmol) and hydroxylamine hydrochloride (119 mg, 1.71 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-formyl-N-3-pyridinylbenzamide (may be prepared as described in Example 82; 300 mg, 0.86 mmol) in methanol (10 ml) and the mixture was stirred at room temperature for 30 min. The mixture was evaporated under reduced pressure to half volume. The mixture was diluted with water (20 ml) and filtered. The solid was washed with cold water (20 ml)/cold methanol (5 ml) and dried under vacuum to yield the title compound as a white solid. 220 mg.

Workup

  1. customThe mixture was evaporated under reduced pressure to half volume
  2. additionThe mixture was diluted with water (20 ml)
  3. filtrationfiltered
  4. washThe solid was washed with cold water (20 ml)/cold methanol (5 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d012fa344e374134a055df893d76495b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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