Potassium Carbonate → HCID 11551613, compound

HRID 2217335Notes

Reaction equation

I.[Cl:2][C:3]1[CH:15]=[CH:14][C:13]2[C:8]3[N:9]=[C:10]([NH2:12])[S:11][C:7]=3[CH2:6][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>O1CCCC1>[Cl:2][C:3]1[CH:15]=[CH:14][C:13]2[C:8]3[N:9]=[C:10]([NH:12][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)[S:11][C:7]=3[CH2:6][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-Chloro-8H-indeno[1,2-d]thiazol-2-ylamine hydroiodide 10 (80 mg; 0.23 mmol), potassium carbonate (138 mg; 1.0 mmol) and isonicotinoyl chloride hydrochloride (89 mg; 0.5 mmol) in dry tetrahydrofuran was heated to 80° C. in a sealed tube. After 20 hr., the mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was diluted with methylene chloride and washed with water. The organic layer was dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was purified by reverse phase HPLC (eluent: acetonitrile/water/0.1% trifluoroacetic acid) to provide 20 mg of N-(6-Chloro-8H-indeno[1,2-d]thiazol-2-yl)-isonicotinamide 11 as the trifluoroacetate salt. EI-HRMS m/e calcd for C16H10ClN3OS (M+) 327.0233, found 327.0217.

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo
additionThe residue was diluted with methylene chloride
washwashed with water
dry with materialThe organic layer was dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by reverse phase HPLC (eluent: acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-ec32207e5cc74350b2a9807183b8cf7d
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407977B2

Reaction notes

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