Tetrahydrofuran → N-(2-methylcyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide

HRID 601994

Reaction equation

HRID 601994 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:15])[C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].O1CCCC1.[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH2:28]>C(N(CC)CC)C>[CH3:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH:28][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([F:1])[C:10]([O:11][CH2:12][C:13]#[CH:14])=[C:9]([F:15])[CH:8]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 234322-MethylcyclohexylamineHCID 574456963,5-Difluoro-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701175N-(2-methylcyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamideYield 64%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 346 mg of 3,5-difluoro-4-(2-propynyloxy)benzoyl chloride and 1 ml of tetrahydrofuran was added dropwise under ice cooling to a mixture of 5 ml of tetrahydrofuran, 170 mg of 2-methylcyclohexylamine and 182 mg of triethylamine. The mixture obtained was stirred at room temperature for 0.5 hour. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 295 mg of N-(2-methylcyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 42 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d5f413be52d40caa5e9e260d2e17b99
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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