Methanesulfonyl chloride → 3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenethyl methanesulfonate

HRID 2410594Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21][CH2:22][OH:23])[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30].CCN(C(C)C)C(C)C.[S:40](Cl)([CH3:43])(=[O:42])=[O:41]>C(Cl)Cl>[CH3:43][S:40]([O:23][CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:12]2[N:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:14][N:13]=2)[CH:16]=1)(=[O:42])=[O:41]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethanol (0.2 mmol) in DCM (2 mL) at 0° C. was added DIEA (71 μL, 0.4 mmol) and mesyl chloride (17 μL, 0.22 mmol). The resulting mixture was stirred at 0° C. for 10 minutes, allowed to warm to RT and stirred for 2 hours. The mixture was diluted with DCM (20 mL) and washed with a saturated aqueous solution of NaHCO3. The aqueous layer was extracted with DCM (3×20 mL). The combined organic fractions were dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was all used in the next step without further purification.

Workup

temperatureto warm to RT
stirringstirred for 2 hours
washwashed with a saturated aqueous solution of NaHCO3
extractionThe aqueous layer was extracted with DCM (3×20 mL)
dry with materialThe combined organic fractions were dried (MgSO4)
filtrationfiltered
customthe solvent removed in vacuo
customall used in the next step without further purification

Sources & evidence

ORD record: ord-d67a14a121764a328688d9f2966b6ec1
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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