Tetrahydrofuran → 5-Ethenyl-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylic acid

HRID 2046408Notes

Reaction equation

[CH:1]([C:3]1[S:7][C:6]([C:8]([O:10]C)=[O:9])=[CH:5][C:4]=1[C:12]1[N:16]2[N:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14][CH:13]=1)=[CH2:2].C1COCC1.[OH-].[K+]>CO>[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][C:4]=1[C:12]1[N:16]2[N:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14][CH:13]=1)=[CH2:2]

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 5-ethenyl-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate (130 mg, 0.456 mmol) was dissolved in methanol (2.28 mL) and THF (2.28 mL) and 1M KOH in MeOH (1.38 mL, 1.38 mmol) was added to the mixture. The solution was left to stir at 60° C. for 18 h. The reaction was cooled to room temperature and concentrated under reduced pressure. 1N HCl was added to the residue and the precipitate filtered. The precipitate was then dried under high vacuum affording the title compound as a yellow solid. 1H NMR (500 MHz, CD3SOCD3) δ 13.37 (s, 1H, br); 8.62 (d, 1H); 8.23 (d, 1H); 8.07 (s, 1H); 7.96 (s, 1H); 7.33 (dd, 1H); 6.91 (dd, 1H); 5.84 (d, 1H); 5.41 (d, 1H). LRMS (APCI) calc'd for (C13H9N3O2S) [M+H]+, 272.0. found 272.0.

Workup

waitThe solution was left
temperatureThe reaction was cooled to room temperature
concentrationconcentrated under reduced pressure
addition1N HCl was added to the residue
filtrationthe precipitate filtered
customThe precipitate was then dried under high vacuum

Sources & evidence

ORD record: ord-cfc9ee13b55242f881bd5418650cef36
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592425B2

Reaction notes

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