Ethyl ketone → HCID 66743631, compound

HRID 2363934Notes

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].[CH3:16][CH2:17][C:18](=O)[CH2:19][CH3:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:17]([C:18]1([CH2:19][CH3:20])[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)[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), 3-pentanone (1.0 mL), p-toluenesulfonic acid monohydrate (0.0096 g, 0.050 mmol) and acetic acid (3.0 mL) was stirred for 3 h at 70° C. The reaction mixture was poured into aqueous sodium hydrogen carbonate (200 mL). Extraction with ethyl acetate (100 mL, 50 mL), washing with aqueous sodium hydrogen carbonate, drying over magnesium sulfate, filtration and concentration at reduced pressure gave a residue, which was purified by column chromatography (40 g, silica, Combiflash, dichloromethane to 90:10 dichloromethane/methanol), then triturated with ethyl acetate. The precipitate was collected by filtration to afford the title compound (0.040 g, 28%) as a yellow solid:

Workup

extractionExtraction with ethyl acetate (100 mL, 50 mL)
washwashing with aqueous sodium hydrogen carbonate
dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
customgave a residue, which
customwas purified by column chromatography (40 g, silica, Combiflash, dichloromethane to 90:10 dichloromethane/methanol)
customtriturated with ethyl acetate
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-b41a1b62e0744d6facf071fb936a514b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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