p-Toluenesulfonic acid → HCID 66744105, compound

HRID 2363989Notes

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].CC1C=[CH:19][C:20](S(O)(=O)=O)=[CH:21][CH:22]=1.C1(=O)CCC1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:19]4([CH2:20][CH2:21][CH2:22]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (110 mg, 0.502 mmol), PTSA (9.5 mg, 0.050 mmol), cyclobutanone (1.0 mL, 13.3 mmol) and acetic acid (1 mL) was stirred at 80° C. for 16 h. Then, the mixture was poured into saturated aqueous NaHCO3 (100 mL). Extraction with EtOAc (100 mL), washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave a yellow solid. This residue was purified by column chromatography (Purif, silica gel, EtOAc to 95:5 EtOAc/MeOH) to afford yellow solid (30 mg). This solid was triturated with EtOAc/hexane and collected by filtration to afford the title compound (25.6 mg, 19%) as a yellow solid:

Workup

extractionExtraction with EtOAc (100 mL)
washwashing with brine
dry with materialdrying over MgSO4, filtration and concentration under reduced pressure
customgave a yellow solid
customThis residue was purified by column chromatography (Purif, silica gel, EtOAc to 95:5 EtOAc/MeOH)

Sources & evidence

ORD record: ord-0f9dcc8c2f1e4e619c446bebbeb3d6be
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691828B2

Reaction notes

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