Benzylamine → HCID 69224197, compound

HRID 2221104Notes

Reaction equation

HRID 2221104 reaction equation
Br[C:2]1[N:3]=[N:4][C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][C:7]=1[CH2:8][C:9](=[CH2:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(C)C>[CH2:24]([N:31]1[C:2]2[N:3]=[N:4][C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:6][C:7]=2[CH2:8][CH:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:17]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 86760662HCID 86760662, compound

Product 1

HCID 69224197HCID 69224197, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of compound 5E, (0.140 g, 0.37 mmol) in 1.5 mL of isopropanol at room temperature under argon was added (in one portion) benzylamine (0.055 mL, 0.50 mmol). After 15 h, the reaction mixture was heated to 65° C. for 4 h and then to 85° C. for 15 h. The reaction mixture was then cooled to room temperature and the solvent removed at reduced pressure. The residue was dissolved in EtOAc and washed once with saturated sodium bicarbonate solution. The organic extract was dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (1:9 Ether/CH2Cl2) provided the title compound, tert-butyl 8-benzyl-3-phenyl-5,6,7,8-tetrahydropyrido[2,3-c]pyridazine-6-carboxylate, as a light yellow solid (0.084 g, 57%). MS [M+H]+: found 402.

Workup

  1. waitto 85° C. for 15 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customthe solvent removed at reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed once with saturated sodium bicarbonate solution
  6. extractionThe organic extract
  7. dry with materialwas dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customPurification by silica gel chromatography (1:9 Ether/CH2Cl2)

Sources & evidence

ORD record
ord-96959816dfbc423fb707efda91fdf9bc
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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