Potassium Carbonate → HCID 66748466, compound

HRID 1747914Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[O:15]=[S:16]1(=[O:33])[CH2:21][CH2:20][N:19]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:18]2=[N:17]1.[OH-].[Na+]>CS(C)=O>[O:12]1[CH2:13][CH2:14][CH:9]([CH2:8][O:32][C:29]2[CH:28]=[CH:27][C:26]([C:25]3[C:18]4=[N:17][S:16](=[O:33])(=[O:15])[CH2:21][CH2:20][N:19]4[CH:22]=[CH:23][CH:24]=3)=[CH:31][CH:30]=2)[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of potassium carbonate (602 mg), 4-(bromomethyl)tetrahydro-2H-pyran (780 mg), 4-(bromomethyl)tetrahydro-2H-pyran (780 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (602 mg) in DMSO (5 mL) was stirred at 130° C. for 3 hr. The mixture was poured into 1N NaOH aq. and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was passed through column chromatography (NH silica gel, eluted with MeOH) to give the title compound (357 mg) as a pale yellow solid.

Workup

extractionextracted with EtOAc
customThe organic layer was separated
washwashed with 1N NaOH aq. and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
washThe residue was passed through column chromatography (NH silica gel, eluted with MeOH)

Sources & evidence

ORD record: ord-e7a518d2ae79419e9fed15ae8d187d5e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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