Potassium Carbonate → HCID 66747659, compound

HRID 2035938Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[O:7]=[S:8]1(=[O:25])[CH2:13][CH2:12][N:11]2[CH2:14][CH2:15][CH2:16][CH:17]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:10]2=[N:9]1.[Cl:26][C:27]1[CH:34]=[C:33](F)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]>CN(C=O)C>[Cl:26][C:27]1[CH:34]=[C:33]([O:24][C:21]2[CH:22]=[CH:23][C:18]([CH:17]3[C:10]4=[N:9][S:8](=[O:7])(=[O:25])[CH2:13][CH2:12][N:11]4[CH2:14][CH2:15][CH2:16]3)=[CH:19][CH:20]=2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (73.9 mg) was added to a mixture of 4-(2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (50 mg) and 2-chloro-4-fluorobenzonitrile (41.6 mg) in DMF (dry) (1 mL). The mixture was stirred at 60° C. under atmosphere overnight. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated. The residue was crystallized from MeCN-THF/IPE to give the title compound (32.2 mg) as colorless crystals.

Workup

customThe mixture was quenched with water
extractionextracted with EtOAc
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
concentrationconcentrated
customThe residue was crystallized from MeCN-THF/IPE

Sources & evidence

ORD record: ord-d89f879f8088490e9df7ed73a516a4d1
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575154B2

Reaction notes

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