Potassium Carbonate → 9-[4-(Cycloheptyloxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405744Notes

Reaction equation

[O:1]=[S:2]1(=[O:19])[CH2:7][CH2:6][N:5]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:4]2=[N:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:27]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[OH-].[Na+]>CS(C)=O.C1COCC1.CCOC(C)=O>[CH:27]1([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]3[C:4]4=[N:3][S:2](=[O:1])(=[O:19])[CH2:7][CH2:6][N:5]4[CH:8]=[CH:9][CH:10]=3)=[CH:13][CH:14]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg), potassium carbonate (390 mg) in DMSO (5 mL) was added bromocycloheptane (250 mg). The mixture was stirred at 130° C. for 1 hr. Another bromocycloheptane (100 uL) was added and the mixture was stirred at room temperature overnight. 0.5 N NaOH aq., EtOAc and THF were added and the extracted organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was crystallized from MeCN/IPE to give the title compound (144 mg) as colorless crystals.

Workup

stirringthe mixture was stirred at room temperature overnight
washthe extracted organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was crystallized from MeCN/IPE

Sources & evidence

ORD record: ord-6f3aafa1af7a491b806ea989e57c01de
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916551B2

Reaction notes

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