Potassium Carbonate → HCID 57665035, compound

HRID 1717426Notes

Reaction equation

CS([O:5][CH2:6][CH2:7][CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[N:12]=[N:11][C:10]=1[C:25]([NH:27][CH:28]1[CH2:30][CH2:29]1)=[O:26])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[F:37][CH:38]([F:41])[CH2:39]O>C(#N)C>[CH:28]1([NH:27][C:25]([C:10]2[N:11]=[N:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)[C:9]=2[CH2:8][CH2:7][CH2:6][O:5][CH2:39][CH:38]([F:41])[F:37])=[O:26])[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 80 °C

Procedure

(4-[(Cyclopropylamino)carbonyl]-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazol-5-yl)propyl methanesulfonate (218 mg, 0.5 mmol) obtained in Example 1201a), potassium carbonate (69 mg, 0.5 mmol, 1.0 eq.) and 2,2-difluoroethanol (0.5 ml) were suspended in acetonitrile (3 ml) and the mixture was stirred at 80° C. for 8 hr. The reaction mixture was concentrated, and chloroform (10 ml) and water (10 ml) were added to the residue. After partitioning, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate) to give the title compound as a white powder (50 mg, 24%).

Workup

concentrationThe reaction mixture was concentrated
additionchloroform (10 ml) and water (10 ml) were added to the residue
customAfter partitioning
dry with materialthe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate)

Sources & evidence

ORD record: ord-3dade8d92e47477e97499a04bdcb8604
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

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