Dichloromethane → HCID 22058437, compound

HRID 497524Notes

Reaction equation

HRID 497524 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[N:19][CH:20]=[C:21]([F:23])[CH:22]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:32]CCl>>[ClH:32].[F:23][C:21]1[CH:20]=[N:19][C:18]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:17]([CH:22]=1)[C:15]([NH:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:16]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 20872664HCID 20872664, compound

Product 1

HCID 22058437HCID 22058437, compound

Procedure

4-{[5-Fluoro-2-(4-fluorophenoxy)-pyridine-3-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (2.58 g, 5.95, mmol) (see Preparation 28) was dissolved in dichloromethane (15 ml) and hydrogen chloride gas bubbled through the solution at 0° C. for 10 minutes. The reaction mixture was then held under an atmosphere of nitrogen at room temperature for a further 45 minutes and the solvent removed in vacuo. The resultant white precipitate was triturated with diethylether (2-fold 10 ml) giving 5-fluoro-2-(4-fluoro-phenoxy)-N-piperidin-4-yl-nicotinamide hydrochloride (2.14 g) as a white solid.

Workup

  1. customhydrogen chloride gas bubbled through the solution at 0° C. for 10 minutes
  2. customthe solvent removed in vacuo
  3. customThe resultant white precipitate was triturated with diethylether (2-fold 10 ml)

Sources & evidence

ORD record
ord-7b3934c8cc0c421baa5d003ec11f288a
Source dataset
uspto-grants-2005_09
Patent number
US06949573B2

Reaction notes

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