Triethylamine → Methanesulfonic acid 2-{4-[5-(2-diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethyl ester

HRID 2069457Notes

Reaction equation

[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]1[N: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(CC)CC.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl.CCOC(C)=O>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4]1[N: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:39]([CH3:38])(=[O:41])=[O:40])=[C:17]([CH2:26][CH3:27])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:28])[N:5]=1)[CH3:30]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 2-{4-[5-(2-diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethanol (895 mg, 2.44 mmol) in DCM (20 mL) is added Et3N (0.47 mL, 3.41 mmol). The reaction mixture is cooled down to 5° C. before adding methanesulfonylchloride (0.23 mL, 2.92 mmol) and stirring is continued at rt for 2 h. The mixture is then diluted with EtOAc and the org. solution is washed with sat. aq. NaHCO3 followed by brine, is dried over MgSO4, filtered and concentrated to give methanesulfonic acid 2-{4-[5-(2-diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-ethyl ester as a brown oil (1.07 g); LC-MS: tR=1.19 min; [M+H]+=489.89.

Workup

washsolution is washed with sat. aq. NaHCO3
dry with materialis dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d406db661dd44f488387f14d8b4f12d2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

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