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6-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine → 7-Cyclobutyl-6-(5,6-dihydro-8H-1,2,4-triazolo[1,5-alpha]pyrazin-7-yl)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine

HRID 277333
Notes
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Reaction equation

HRID 277333 reaction equation
Cl[C:2]1[C:3]([CH:17]2[CH2:20][CH2:19][CH2:18]2)=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.[N:21]1[CH:22]=[N:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][C:25]=12>CS(C)=O>[CH:17]1([C:3]2[C:2]([N:27]3[CH2:28][CH2:29][N:24]4[N:23]=[CH:22][N:21]=[C:25]4[CH2:26]3)=[N:7][N:6]3[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:9][N:10]=[C:5]3[CH:4]=2)[CH2:20][CH2:19][CH2:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 110005936-Chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazineHCID 184069195H,6H,7H,8H-(1,2,4)triazolo(1,5-a)pyrazine

Product 1

HCID 541615477-Cyclobutyl-6-(5,6-dihydro-8H-1,2,4-triazolo[1,5-alpha]pyrazin-7-yl)-3-phenyl-1,2,4-triazolo[4,3-b]pyridazineYield 26.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-chloro-7-cyclobutyl-3-phenyl-1,2,4-triazolo[4,3-b]pyridazine (150 mg, 0.53 mmol) and 5,6,7,8-tetrahydro-1,2,4-triazolo[1,5-α]pyrazine (190 mg, 1.53 mmol) in dimethyl sulphoxide (1 ml) was stirred and heated at 150° C. for 20 hours. The mixture was partitioned between dichloromethane and water. The aqueous phase was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 3→4% methanol-dichloromethane to give the title compound (52 mg, 26%) as an off-white solid (after trituration with diethyl ether). 1H NMR (360 MHz, CDCl3) δ 2.00-2.28 (4H, m), 2.48-2.55 (2H, m), 3.68-3.80 (3H, m), 4.43 (2H, t, J=5.5 Hz), 4.67 (2H, s), 7.46-7.56 (3H, m), 7.97 (1H, s), 8.09 (1H, s),8.37 (2H, br d, J=8 Hz); MS (ES+) m/e 373 [MH]+.

Workup

  1. customThe mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous phase was further extracted with dichloromethane (x2)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with 3→4% methanol-dichloromethane

Sources & evidence

ORD record
ord-983a399c0c574c15a5e782ea01d8e685
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06355798B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes