Potassium Carbonate → HCID 66748466, compound

HRID 2035801Notes

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-7985a3a74a934e0eb02a3c71e07528b0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575154B2

Reaction notes

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