Ammonium Chloride → N-(2-chlorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide

HRID 602005

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([F:21])[C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:5]([N:7]1[CH:13]2[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]2)=[O:6].[Cl-:22].[NH4+]>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[Cl:22][CH:13]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[NH:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([F:1])[C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:15]([F:21])[CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4 ml of chloroform and 298 mg of zinc (II) chloride was stirred at 60° C. After 5 minutes, a mixture of 291 mg of 7-[3,5-difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane and 2 ml of chloroform was added dropwise thereto at 60° C., and the resulting mixture was heated under reflux for 5 hours. Then, an aqueous saturated ammonium chloride solution was added to the reaction mixture, and this was extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.22 g of N-(2-chlorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 87 of the present invention) represented by the formula:

Workup

additionwas added dropwise
temperatureat 60° C., and the resulting mixture was heated
temperatureunder reflux for 5 hours
extractionthis was extracted with chloroform
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9c87c08183054d25addd37cb2ab63ce0
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902400B2

Linked notes

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