Potassium Carbonate → HCID 10214675, compound

HRID 1179127Notes

Reaction equation

HRID 1179127 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69056013HCID 69056013, compoundHCID 178512453HCID 178512453, compound

Product 1

HCID 10214675HCID 10214675, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 disolved 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

  1. temperatureThe mixture was cooled to RT
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customtriturated with diethylether

Sources & evidence

ORD record
ord-ecfbd195c85c4b4483643fe4447a6646
Source dataset
uspto-grants-2007_10
Patent number
US07279473B2

Reaction notes

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