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Cyclopropylacetylene → (6-(5-Cyclopropylisoxazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine

HRID 40395
Notes
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Reaction equation

HRID 40395 reaction equation
Cl/[C:2](=[N:21]\[OH:22])/[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13]C(=O)OC(C)(C)C)=[N:10][N:11]=2)[N:8]=1.[C:23]([CH:25]1[CH2:27][CH2:26]1)#[CH:24].C(=O)([O-])O.[K+]>CCOC(C)=O>[CH:25]1([C:23]2[O:22][N:21]=[C:2]([C:3]3[CH:4]=[CH:5][C:6]4[N:7]([C:9]([CH2:12][NH2:13])=[N:10][N:11]=4)[N:8]=3)[CH:24]=2)[CH2:27][CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 138823CyclopropylacetyleneHCID 516893Potassium BicarbonateHCID 135987468Tert-butyl (z)-((6-(chloro(hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)carbamate

Product 1

HCID 57691172(6-(5-Cyclopropylisoxazol-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamineYield 23.2%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

Dissolved (Z)-tert-butyl (6-(chloro(hydroxyimino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (110 mg, 337 μmol), ethynylcyclopropane (28 μl, 337 μmol), and potassium hydrogencarbonate (67.4 mg, 673 μmol) in 0.3 mL of EtOAc and heated to 60° C. for 12 h to afford the protected intermediate. The solvent was removed by rotary evaporation and the residue was redissolved in dicholoromethane (5 mL) and TFA (2 mL) and stirred for 30 min at room temperature. The solvent was then removed and the residue was redissolved in MeOH. Solid K2CO3 was added and the mixture was stirred for 1 h to free base the title compound. Purified the amine via MPLC (DCM/MeOH+1% NH4OH) to afford the title compound (20 mg, 23% yield).

Workup

  1. customto afford the protected intermediate
  2. customThe solvent was removed by rotary evaporation
  3. dissolutionthe residue was redissolved in dicholoromethane (5 mL) and TFA (2 mL)
  4. customThe solvent was then removed
  5. dissolutionthe residue was redissolved in MeOH
  6. additionSolid K2CO3 was added
  7. stirringthe mixture was stirred for 1 h to free base the title compound
  8. customPurified the amine via MPLC (DCM/MeOH+1% NH4OH)

Sources & evidence

ORD record
ord-9b2ff99cc9894567a238340229554b83
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524900B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes