5-(4-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole → 2-(4-(6-(1-(3-Isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yloxy)-5-methylpyrimidin-4-yloxy)phenyl)propane-1,3-diol

HRID 1619442Notes

Reaction equation

CC1(C)[O:7][CH2:6][CH:5]([C:8]2[CH:36]=[CH:35][C:11]([O:12][C:13]3[N:18]=[CH:17][N:16]=[C:15]([O:19][CH:20]4[CH2:25][CH2:24][N:23]([C:26]5[O:30][N:29]=[C:28]([CH:31]([CH3:33])[CH3:32])[N:27]=5)[CH2:22][CH2:21]4)[C:14]=3[CH3:34])=[CH:10][CH:9]=2)[CH2:4][O:3]1>CC(C)=O>[CH:31]([C:28]1[N:27]=[C:26]([N:23]2[CH2:22][CH2:21][CH:20]([O:19][C:15]3[N:16]=[CH:17][N:18]=[C:13]([O:12][C:11]4[CH:10]=[CH:9][C:8]([CH:5]([CH2:4][OH:3])[CH2:6][OH:7])=[CH:36][CH:35]=4)[C:14]=3[CH3:34])[CH2:25][CH2:24]2)[O:30][N:29]=1)([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 27 °C

Procedure

To a solution of 5-(4-(6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-methylpyrimidin-4-yloxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole (500 mg, 0.0095 moles) in acetone (10 ml) conc. HCl (3 ml) was added portion-wise and reaction mixture was stirred for 2 hours at 27° C. The reaction mixture was concentrated and residue was dissolved in ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 360 mg product as white solid.

Workup

customportion-wise and reaction mixture
concentrationThe reaction mixture was concentrated
dissolutionresidue was dissolved in ethyl acetate
extractionThe organic extract
washwas successively washed with water & brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-3aa1c150ad544c7a841e600186157fa2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772302B2

Reaction notes

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