Methyl Ethyl Ketone → HCID 66743480, compound

HRID 2363955Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([NH2:16])=O.[CH3:17][C:18](=O)[CH2:19][CH3:20].[OH2:22].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:19]([C:18]1([CH3:17])[N:2]([CH3:1])[C:3]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[S:5][C:4]=2[C:14](=[O:22])[NH:16]1)[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-(methylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.094 g, 0.40 mmol), 2-butanone (3.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 3 days at 70° C. in a sealed tube. 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. The oil was purified by column chromatography (Combiflash, 12 g silica gel, hexanes to ethyl acetate), then triturated with ethyl acetate-hexanes (1:1), and the precipitate was collected by filtration to afford the title compound (0.0578 g, 63%) as a yellow solid:

Workup

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
customThe oil was purified by column chromatography (Combiflash, 12 g silica gel, hexanes to ethyl acetate)
customtriturated with ethyl acetate-hexanes (1:1)
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-806b3cb67d5841d9b55abfc184603d20
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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