Water → HCID 66748986, compound

HRID 1747920Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of potassium carbonate (450 mg), (iodomethyl)cyclopentane (684 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) in DMSO (5 mL) was stirred at 130° C. for 2 hr. The mixture was poured into water 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 washed with Et2O to give the title compound (311 mg) as a pale yellow solid. The solid was crystallized from CH3CN-IPE to give 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 washed with Et2O

Sources & evidence

ORD record: ord-1510985160014cbd932b6ed9cc773d60
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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