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

HRID 602009

Reaction equation

HRID 602009 reaction equation
[F-:1].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:21]=[C:22]([CH:32]=[C:33]([F:39])[C:34]=1[O:35][CH2:36][C:37]#[CH:38])[C:23]([N:25]1[CH:31]2[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:24].[Cl-].[NH4+]>O1CCCC1>[F:1][CH:31]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[NH:25][C:23](=[O:24])[C:22]1[CH:21]=[C:20]([F:19])[C:34]([O:35][CH2:36][C:37]#[CH:38])=[C:33]([F:39])[CH:32]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 577011787-[3,5-Difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane

Product 1

HCID 57701160N-(2-fluorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At room temperature, 1.2 ml of tetrabutylammonium fluoride (1M tetrahydrofuran solution) was added dropwise to a mixture of 4 ml of tetrahydrofuran and 291 mg of 7-[3,5-difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane. This mixture was stirred at room temperature for 1 hour. Then, an aqueous saturated ammonium chloride solution was added to the reaction mixture, and this was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of N-(2-fluorocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 114 of the present invention) represented by the formula:

Workup

  1. extractionthis was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ebb46a477594e94aef8da3044244e9a
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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