Triethylamine → N-((1S)-1-cyclohexylethyl)-3-fluoro-4-(2-propynyloxy)benzamide

HRID 601993

Reaction equation

HRID 601993 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].[CH:15]1([C@@H:21]([NH2:23])[CH3:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:15]1([C@@H:21]([NH:23][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]#[CH:14])=[C:2]([F:1])[CH:3]=2)[CH3:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5325951(S)-(+)-1-CyclohexylethylamineHCID 574456843-Fluoro-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701210N-((1S)-1-cyclohexylethyl)-3-fluoro-4-(2-propynyloxy)benzamideYield 86.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 5 ml of ethyl acetate and 0.30 g of 3-fluoro-4-(2-propynyloxy)benzoyl chloride were added 0.22 g of (1S)-1-(cyclohexyl)ethylamine and 0.20 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 1 hour. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was washed with hexane to obtain 0.37 g of N-((1S)-1-cyclohexylethyl)-3-fluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 37 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-2a5bf7b9c734421d8ef49376c9eceadf
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Linked notes

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