Ethanol → HCID 58137740, compound

HRID 2189464Notes

Reaction equation

HRID 2189464 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[N:20]=[C:21](Cl)[CH:22]=[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCO.CC([O-])=O.[Na+]>[Pd].CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]3[N:20]=[CH:21][CH:22]=[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 517045Sodium AcetateHCID 58137757HCID 58137757, compound

Product 1

HCID 58137740HCID 58137740, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 3-(4-(tert-butoxycarbonylamino)phenyl)-6-chloro-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate (66D) (300 mg, 0.67 mmol) in a mixed solvent of EtOH (4 mL) and MeOH (1 mL) was bubbled through argon for 5 min, and then NaOAc (66.2 mg, 0.81 mmol) was added, followed by 5% Pd/C (50 mg). The vessel was evacuated and flashed with H2 gas three times and stirred under H2 (1 atm) for 1 h. Analysis by LC/MS indicated the starting material was consumed. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure. The obtained crude residue was purified using a silica gel cartridge (40 g) eluting with a gradient of EtOAc (0-100%) in hexanes to afford 150 mg (54%) of the title compound as a yellow foam. HPLC/MS (Method B): retention time=3.02 min, [M+H]+=412.3.

Workup

  1. customThe vessel was evacuated
  2. customwas consumed
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe obtained crude residue
  6. customwas purified
  7. washeluting with a gradient of EtOAc (0-100%) in hexanes

Sources & evidence

ORD record
ord-a3d26deefc8d4b54adb68cb373e40580
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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