Diethyl Pyrocarbonate → 3-(4-tert-Butylphenyl)propynoic Acid N-[1-(3-fluoro-4-methanesulfonylamino-5-vinylphenyl)ethyl]amide

HRID 2358394Notes

Reaction equation

HRID 2358394 reaction equation
[NH2:1][CH:2]([C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[C:6]([F:17])[CH:5]=1)[CH3:3].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][C:30](O)=[O:31])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].CCOC(OC(OCC)=O)=O>CN(C=O)C>[F:17][C:6]1[CH:5]=[C:4]([CH:2]([NH:1][C:30](=[O:31])[C:29]#[C:28][C:25]2[CH:26]=[CH:27][C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:23][CH:24]=2)[CH3:3])[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 3051Diethyl PyrocarbonateHCID 113447013-(4-tert-butylphenyl)prop-2-ynoic AcidHCID 68455310N-[4-(1-Aminoethyl)-2-fluoro-6-vinylphenyl]methanesulfonamide

Product 1

HCID 118525783-(4-tert-Butylphenyl)propynoic Acid N-[1-(3-fluoro-4-methanesulfonylamino-5-vinylphenyl)ethyl]amideYield 95.09%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(1-Amino-ethyl)-2-fluoro-6-vinylphenyl]methanesulfonamide (0.03 mmol, 10.0 mg), (4-tert-butylphenyl)propynoic acid (step 2 of Example 11, 0.03 mmol, 6.52 mg), DEPC (0.03 mmol, 5.46 μl), and TEA (0.06 mmol, 8.36 μl) were added into DMF. The mixture was stirred for 12 hr. The reaction mixture was purified according to Example 12 to give a title product (11.3 mg, 95.09%).

Workup

  1. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-9a48bb2f719142fbabf17f3da134e125
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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