Potassium Carbonate → HCID 10214675, compound

HRID 729344Notes

Reaction equation

CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:8]([CH3:16])=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[N:11]2)=O.[CH:18]1([NH:21][C:22]([NH2:24])=[NH:23])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:18]1([NH:21][C:22]2[N:24]=[C:5]([C:7]3[C:8]([CH3:16])=[N:9][N:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[N:11]4)[CH:4]=[CH:3][N:23]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution (2E)-3-(dimethylamino)-1-(2-methylpyrazolo[1,5-b]pyridazin-3-yl)-2-propen-1-one (50 mg, 0.22 mmol) in DMF (2.5 mL) was added N-cyclopropylguanidine.0.5H2SO4 (130 mg, 0.66 mmol) and potassium carbonate (152 mg, 1.10 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 dissolved in CH2Cl2 and triturated with diethylether to give the title compound as a yellow solid (22 mg, 38%). 1H-NMR (300 MHz, CDCl3) δ 9.02 (d, 1H, J=8.8 Hz), 8.39 (d, 1H, J=5.2 Hz), 8.35 (dd, 1H, J=4.4, 2.0 Hz), 7.15 (dd, 1H, J=8.8, 4.4 Hz), 6.94 (d, 1H, J=5.3 Hz), 5.45 (s, 1H), 2.89 (m, 1H), 2.83 (s, 3H), 0.91 (m, 2H), 0.68 (m, 2H); MS (ESI) (M+H)+ 267.

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
dissolutionthen dissolved in CH2Cl2
customtriturated with diethylether

Sources & evidence

ORD record: ord-ec28d055673d43eba305bf6539cb3447
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582630B2

Reaction notes

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