Methanesulfonyl chloride → HCID 86640601, compound

HRID 2047326Notes

Reaction equation

HRID 2047326 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[C:23]([CH3:25])[C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH2:26][CH3:27])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:28])[N:5]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.CC(=O)OCC>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[C:23]([CH3:25])[C:18]([O:19][CH2:20][CH2:21][O:22][S:41]([CH3:40])(=[O:43])=[O:42])=[C:17]([CH2:26][CH3:27])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:28])[N:5]=1)[CH3:30]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68578477HCID 68578477, compound

Product 1

HCID 86640601HCID 86640601, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethanol (850 mg, 2.07 mmol) and DIPEA (401 mg, 3.11 mmol) in DCM (20 mL), methane sulfonylchloride (285 mg, 2.49 mmol) is slowly added. The mixture is stirred at rt for 30 min before it is diluted with EA and washed with sat. aq. NaHCO3-solution. The washing is extracted back three times with EA. The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give crude methanesulfonic acid 2-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethyl ester (925 mg) as a yellow solid; LC-MS: tR=0.94 min; [M+1]+=489.18.

Workup

  1. washwashed with sat. aq. NaHCO3-solution
  2. extractionThe washing is extracted back three times with EA
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried

Sources & evidence

ORD record
ord-b99b8b7c00f94c549ee488b46f421c8e
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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