Hydrochloric Acid → 4-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide

HRID 1053166Notes

Reaction equation

HRID 1053166 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:12])[CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]=1.N1C=CC=CC=1.Cl>ClCCl>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:21][C:19]2[CH:18]=[CH:17][N:16]=[C:15]([O:14][CH3:13])[CH:20]=2)=[O:7])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 2808912-Methoxypyridin-4-amineHCID 27364984-Chloro-2,5-difluorobenzoyl chloride

Product 1

HCID 867284804-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-2,5-difluoro-benzoyl chloride (5 g, 23.70 mmol) in dichloromethane (25 mL) was added dropwise to a mixture of 2-methoxypyridin-4-amine (2.94 g, 23.70 mmol), pyridine (5.75 mL, 71.10 mmol) and dichloromethane (100.0 mL) at 0° C. The mixture was allowed to warm to room temperature and was stirred at that temperature for 43 hours. The mixture was poured into 1N HCl (50 mL). The mixture was filtered using dichloromethane and the solid was isolated. The solid was dried under vacuum to yield 4-chloro-2,5-difluoro-N-(2-methoxy-4-pyridyl)benzamide (6.2 g, 88%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ 10.89 (s, 1H), 8.16-8.05 (m, 1H), 7.97-7.75 (m, 2H), 7.29-7.15 (m, 2H), 3.85 (s, 3H) ppm. ESI-MS m/z calc. 298.03. found 299.3 (M+1)+; Retention time: 1.43 minutes (3 minutes run).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solid was isolated
  3. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-82d1927c6b9948748506d725e2c73a3b
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

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