4-((4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)methyl)-2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazole → 2-(4-((2-(1-(Pyrimidin-2-yl)piperidin-4-yl)thiazol-4-yl)methoxy)phenyl)propane-1,3-diol

HRID 1619447Notes

Reaction equation

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

Participants

Conditions

Temperature: 27 °C

Procedure

To a solution of 4-((4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)methyl)-2-(1-(pyrimidin-2-yl)piperidin-4-yl)thiazole (500 mg, 0.0010 moles) in acetone (20 ml), conc. HCl (2 ml) was added portion-wise and the reaction mixture was stirred for 12 hours at 27° C. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The organic layer was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 500 mg product as white solid

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in ethyl acetate
washThe organic layer was successively washed with water & brine
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-0b867fc9a9834705914604ef64f1fc01
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772302B2

Reaction notes

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