Triethylamine → HCID 22276972, compound

HRID 1063929Notes

Reaction equation

HRID 1063929 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:34])[CH2:10][C:11]1([C:28]2[S:29][C:30](Br)=[CH:31][CH:32]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1.C(N(CC)CC)C.[C:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)#[CH:43]>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:34])[CH2:10][C:11]1([C:28]2[S:29][C:30]([C:43]#[C:42][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:31][CH:32]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 22276500HCID 22276500, compound

Product 1

HCID 22276972HCID 22276972, compoundYield 110.9%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of N-(2-tetrahydropyranyloxy)-2-[7-(5-bromo-2-thienyl)-4-benzoyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (200 mg), palladium(II) acetate (1.57 mg), triphenylphosphine (7.34 mg), copper(II) iodide (6.7 mg) and triethylamine (106 mg) in dimethylformamide was added ethynylbenzene (46.5 mg) at room temperature under nitrogen. After stirring for 2 hours at 60° C., the mixture was diluted with ethyl acetate, washed with 3% aqueous sodium bicarbonate and brine, dried over sodium sulfate and filtered. The obtained filtrate was concentrated and purified by column chromatography on silica gel (eluent: 0-2% methanol in chloroform) to give N-(2-tetrahydropyranyloxy)-2-[7-(5-(2-phenylethynyl)-2-thienyl)-4-benzoyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (230 mg) as yellow amorphous solid.

Workup

  1. washwashed with 3% aqueous sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe obtained filtrate was concentrated
  5. custompurified by column chromatography on silica gel (eluent: 0-2% methanol in chloroform)

Sources & evidence

ORD record
ord-a5e8465a7229474098f43808e441f498
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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