Sodium Bicarbonate → HCID 66743837, compound

HRID 2363957Notes

Reaction equation

[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[F:16][C:17]([F:23])([F:22])[CH2:18][C:19](=O)[CH3:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:20][C:19]1([CH2:18][C:17]([F:23])([F:22])[F:16])[NH:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=3)[S:4][C:3]=2[C:13](=[O:14])[NH:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), 4,4,4-trifluoro-2-butanone (2.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (3.0 mL) was stirred for 2 h at 70° C. in a sealed tube. The mixture was heated to 80° C. After 3 days, the mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate-tetrahydrofuran (2:1, 100 mL, 50 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, 12 g silica gel, dichloromethane to ethyl acetate), then triturated with ethyl acetate-hexanes (1:1), and the precipitate was collected by filtration to afford the title compound (0.0249 g, 15%) as a yellow solid:

Workup

temperatureThe mixture was heated to 80° C
waitAfter 3 days
extractionExtraction with ethyl acetate-tetrahydrofuran (2:1, 100 mL, 50 mL)
dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
customgave an oil
customThis oil was purified by column chromatography (Combiflash, 12 g silica gel, dichloromethane to ethyl acetate)
customtriturated with ethyl acetate-hexanes (1:1)
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-191d46adbb35435b8f45340dfe9cfcba
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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