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

HRID 2168793Notes

Reaction equation

HRID 2168793 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-(4-cyclohexyloxy-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 0.1N 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 0.1N 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-d8f50caf297a40dd9c44fb07abd1e027
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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