Triethylamine → [6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yl]-methanone

HRID 402065Notes

Reaction equation

HRID 402065 reaction equation
N(C[C@H]1CCNC[C@H]1O)=[N+]=[N-].C(N(CC)CC)C.FC1C([O:26][C:27]([C:29]2[N:30]=[N:31][C:32]([CH2:48][CH2:49][CH2:50][CH3:51])=[C:33]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]4)=[CH:37][CH:36]=3)[CH:34]=2)=O)=C(F)C(F)=C(F)C=1F.CCOC(C)=O>COCCOC>[CH2:48]([C:32]1[N:31]=[N:30][C:29]([CH:27]=[O:26])=[CH:34][C:33]=1[C:35]1[CH:36]=[CH:37][C:38]([O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:39][CH:40]=1)[CH2:49][CH2:50][CH3:51]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 866578236-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl esterHCID 86657829cis-4-Azidomethyl-piperidin-3-ol

Product 1

HCID 86657831[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yl]-methanoneYield 37.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of cis-4-azidomethyl-piperidin-3-ol (1.4 mmol, 272 mg) in DME (4.2 mL) was added triethylamine (5.62 mmol, 0.8 mL) and 6-butyl-5-(4cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester (1.41 mmol, 785 mg). Reaction was stirred at room temperature for 3 h. Upon completion, the reaction was quenched with 0.1 N NaOH (40 mL), extracted, dried and removal of solvent afforded the residue which was chromatographed with hexane:EtOAc gradient to afforded (+)-cis-4-azidomethyl-3-hydroxy-piperidin-1-yl)-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yl]-methanone (180 mg, 25% yield).

Workup

  1. customReaction
  2. customUpon completion, the reaction was quenched with 0.1 N NaOH (40 mL)
  3. extractionextracted
  4. customdried
  5. customremoval of solvent
  6. customafforded the residue which
  7. customwas chromatographed with hexane

Sources & evidence

ORD record
ord-4bd57510551e4d4786a7b51353536c04
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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