Ethyl Acetate → HCID 67053852, compound

HRID 2408487Notes

Reaction equation

HRID 2408487 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].Cl[C:18]1[N:23]=[N:22][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:20]2[S:29][C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=3)=[CH:31][C:19]=12.CCOC(C)=O>CN1C(=O)CCC1>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([O:1][C:18]2[N:23]=[N:22][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:20]3[S:29][C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=4)=[CH:31][C:19]=23)[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 5456991-Boc-3-hydroxypiperidineHCID 86670628HCID 86670628, compound

Product 1

HCID 67053852HCID 67053852, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

tert-Butyl 3-hydroxypiperidine-1-carboxylate (100 mg, 0.5 mmol) was dissolved in dry NMP (5 mL) and NaH (20 mg, 60% in oil, 0.5 mmol) was added carefully. The mixture was stirred at room temperature for 10 min. Then, ethyl 4-chloro-2-(3-fluorophenyl)thieno[2,3-d]pyridazine-7-carboxylate (130 mg, 0.5 mmol) was added. The mixture was heated up to 80° C. and stirred for 30 min. After cooling to room temperature, EtOAc was added to dilute the reaction and washed with water and brine. The organics was dried over Na2SO4 and filtered, concentrated. The crude product was purified with column (silica gel) to give the product ethyl 4-(1-(tert-butoxycarbonyl)piperidin-3-yloxy)-2-(3-fluorophenyl)thieno[2,3-d]pyridazine-7-carboxylate (151 mg). HPLC-MS tR=2.17 min (UV254 nm); mass calculated for formula C25H28FN3O5S 501.2, observed LCMS m/z 502.2 (M+H).

Workup

  1. temperatureThe mixture was heated up to 80° C.
  2. stirringstirred for 30 min
  3. temperatureAfter cooling to room temperature
  4. additionto dilute
  5. customthe reaction
  6. washwashed with water and brine
  7. dry with materialThe organics was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified with column (silica gel)

Sources & evidence

ORD record
ord-1282a46b5a964bf58b2bdb017c92a650
Source dataset
uspto-grants-2014_08
Patent number
US08815863B2

Reaction notes

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