Potassium Carbonate → HCID 10171618, compound

HRID 729345Notes

Reaction equation

CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:8]([CH2:16][CH3:17])=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[N:11]2)=O.[CH:19]1([NH:22][C:23]([NH2:25])=[NH:24])[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:19]1([NH:22][C:23]2[N:25]=[C:5]([C:7]3[C:8]([CH2:16][CH3:17])=[N:9][N:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[N:11]4)[CH:4]=[CH:3][N:24]=2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution (2E)-3-(dimethylamino)-1-(2-ethylpyrazolo[1,5-b]pyridazin-3-yl)-2-propen-1-one (75 mg, 0.31 mmol) in DMF (2.0 mL) was added N-cyclopropylguanidine.0.5H2SO4 (181 mg, 0.92 mmol) and potassium carbonate (212 mg, 1.54 mmol). The reaction was heated at an oil bath temperature of 135° C. for about 18 hours. The mixture was cooled to RT and the solvent was removed in vacuo. The residue was dissolved in chloroform and filtered. The filtrate was concentrated in vacuo then disolved in CH2Cl2 and triturated with diethylether and hexanes to give the title compound as an orange solid (32 mg, 36%). 1H-NMR (300 MHz, CDCl3) δ 8.96 (d, 1H, J=8.7 Hz), 8.38 (d, 1H, J=5.4 Hz), 8.34 (dd, 1H, J=4.4, 1.9 Hz), 7.14 (dd, 1H, J=9.0, 4.5 Hz), 6.92 (d, 1H, J=5.4 Hz), 5.47 (s, 1H), 3.23 (q, 2H, J=7.5 Hz), 2.88 (m, 1H), 1.50 (t, 3H, J=7.5 Hz), 0.91 (m, 2H), 0.67 (m, 2H); MS (ESI) (M+H)+ 281.

Workup

temperatureThe mixture was cooled to RT
customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in chloroform
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customtriturated with diethylether and hexanes

Sources & evidence

ORD record: ord-cba214baa308485d870ee50f4a356343
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582630B2

Reaction notes

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