Methanesulfonyl chloride → 2-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate

HRID 2278780Notes

Reaction equation

HRID 2278780 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:26]=[C:25]([CH3:27])[C:20]([O:21][CH2:22][CH2:23][OH:24])=[C:19]([CH2:28][CH3:29])[CH:18]=4)[N:13]=3)[CH:9]=[C:8]([O:30][CH3:31])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C1COCC1.CC(=O)OCC>[CH3:41][S:42]([O:24][CH2:23][CH2:22][O:21][C:20]1[C:25]([CH3:27])=[CH:26][C:17]([C:14]2[N:13]=[C:12]([C:10]3[CH:9]=[C:8]([O:30][CH3:31])[N:7]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:11]=3)[O:16][N:15]=2)=[CH:18][C:19]=1[CH2:28][CH3:29])(=[O:44])=[O:43]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 705581362-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethanol

Product 1

HCID 867020182-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonateYield 96.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethanol (638 mg, 1.51 mmol) in THF, DIPEA (389 mg, 3.01 mmol) is added. The mixture is cooled to 0° C. before methanesulfonyl chloride (207 mg, 1.81 mmol) is added. The mixture is stirred at rt for 30 min before it is diluted with EA (100 mL) and washed with sat. aq. NaHCO3 solution (50 mL) and brine (50 mL). The org. extract is dried over MgSO4, filtered and concentrated to give 2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate (733 mg) as a yellow oil; LC-MS: tR=1.19 min, [M+H]+=502.05.

Workup

  1. additionis added
  2. washwashed with sat. aq. NaHCO3 solution (50 mL) and brine (50 mL)
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-07fec1059993482b9db5bcd1501c3165
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

Loading…