3,6-Dichloropyridazine → Tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

HRID 873566Notes

Reaction equation

HRID 873566 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[O:6])[CH2:2]1.C(N(C(C)C)CC)(C)C.[Cl:36][C:37]1[N:38]=[N:39][C:40](Cl)=[CH:41][CH:42]=1>C(O)C>[Cl:36][C:37]1[N:38]=[N:39][C:40]([N:1]2[CH2:4][CH:3]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([CH:14]4[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]4)=[CH:10][CH:9]=3)=[O:6])[CH2:2]2)=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 673313,6-DichloropyridazineHCID 81531DiisopropylethylamineHCID 86702043HCID 86702043, compound

Product 1

HCID 86702042Tert-butyl 4-(4-(1-(6-chloropyridazin-3-yl)azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

In a 50 mL round-bottomed flask was added tert-butyl 4-(4-(azetidine-3-carboxamido)phenyl)piperidine-1-carboxylate (918 mg, 2.55 mmol) and diisopropylethylamine (0.558 ml, 3.19 mmol) in ethanol (10.6 ml). 3,6-dichloropyridazine (317 mg, 2.128 mmol) was added as a solid in a single portion. The reaction was stirred overnight at 45° C.; and the reaction was cooled and concentrated. Dichloromethane and water were added and the layers were separated. The aqueous layer was extracted three times with dichloromethane and the combined organics were dried with magnesium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography to give the title compound.

Workup

  1. temperatureand the reaction was cooled
  2. concentrationconcentrated
  3. additionDichloromethane and water were added
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted three times with dichloromethane
  6. dry with materialthe combined organics were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by regular phase flash column chromatography

Sources & evidence

ORD record
ord-ef4b77b9051e4133a176093c0841bda9
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

Loading…