1,1'-Carbonyldiimidazole → N-[1-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl]-methanesulfonamide

HRID 1529128Notes

Reaction equation

HRID 1529128 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][S:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4([C:32]([OH:34])=O)[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[O:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:47][S:48]([NH2:51])(=[O:50])=[O:49].CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:1][C:2]1[C:6]([CH2:7][S:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4([C:32]([NH:51][S:48]([CH3:47])(=[O:50])=[O:49])=[O:34])[CH2:30][CH2:31]4)=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)[O:4][N:3]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 513523511-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid

Product 1

HCID 51352174N-[1-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl]-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-[4′-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid (0.2 g, 0.43 mmol) was dissolved in dioxane along with carbonyldiimidazole (0.2 g, 1.23 mmol), methanesulfonamide (0.14 g, 1.47 mmol) and Hünig's base. The reaction was heated to reflux overnight then cooled and submitted to standard aqueous workup. The residue was purified via silica gel chromatography (0-60% EtOAc in hexanes) to give the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. temperaturethen cooled
  4. customThe residue was purified via silica gel chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7200b58c242f490a955d80447a4ad335
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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