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Potassium Carbonate → (+/-)-2-(trans-2-Hydroxycyclohexyl)-5-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one

HRID 2067111
Notes
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Reaction equation

HRID 2067111 reaction equation
C[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:20]2[N:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18](=S)[C:17]([C:26](OCC)=[O:27])=[N:16]1.[NH:31]([C@@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[OH:39])[NH2:32].[C:40](=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>C(O)C.[Hg](Cl)Cl>[OH:39][C@@H:34]1[CH2:35][CH2:36][CH2:37][CH2:38][C@H:33]1[N:31]1[C:26](=[O:27])[C:17]2=[N:16][N:15]([CH2:14][C:3]3[CH:4]=[CH:5][C:6]([C:8]4[CH:9]=[N:10][C:11]([CH3:40])=[CH:12][CH:13]=4)=[N:7][CH:2]=3)[C:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18]2=[N:32]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 13403698trans-2-HydrazinocyclohexanolHCID 86662100Ethyl 1-[(6-methyl-2,3'-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

Product 1

HCID 49763347(+/-)-2-(trans-2-Hydroxycyclohexyl)-5-[(6'-methyl-2,3'-bipyridin-5-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 1-[(6-methyl-2,3′-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate [(Example 6, Step 2), 47 mg, 0.11 mmol], (±)-trans-2-hydrazinocyclohexanol (44 mg, 0.34 mmol, 3 equiv), potassium carbonate (0.16 g, 1.1 mmol, 10 equiv) and mercury(II) chloride (31 mg, 0.11 mmol, 1 equiv) were combined in ethanol (10 mL) at ambient temperature and after 5 minutes, the mixture was warmed to 70° C. for 3 h. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (100 mL, aqueous saturated) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative TLC (eluting with ethyl acetate containing 10% methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 9.02 (1H, d, J=2.1 Hz), 8.93 (1H, d, J=2.0 Hz), 8.75 (1H, dd, J=4.6, 1.8 Hz), 8.52 (1H, dd, J=8.1, 1.8 Hz), 8.16 (1H, dd, J=8.2, 2.4 Hz), 7.97 (1H, dd, J=8.3, 2.3 Hz), 7.66 (1H, dd, J=8.2, 0.6 Hz), 7.50 (1H, dd, J=8.0, 4.6 Hz), 7.23 (1H, d, J=8.0 Hz), 6.0 (1H, d, J=14.3 Hz), 5.96 (1H, d, J=14.3 Hz), 4.30 (1H, ddd, J=11.7, 9.8, 4.1 Hz), 4.07-4.01 (1H, m,), 2.60 (3H, s), 2.20 (1H, br d, J=10.3 Hz), 2.01 (1H, br d, J=11.9 Hz), 1.89-1.79 (2H, m), 1.72-1.53 (2H, m), 1.50-1.39 (2H, m) ppm; high resolution mass spectrometry (ES+) m/z 468.2142 [(M+H)+; calculated for C26H26N7O2: 468.2143].

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate (3×75 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (eluting with ethyl acetate containing 10% methanol)

Sources & evidence

ORD record
ord-aacd68996f694bbf9f071495728de00a
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293744B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes