2-Naphthalenesulfonyl chloride → HCID 46681463, compound

HRID 1675047Notes

Reaction equation

HRID 1675047 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[N:15]1([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([C:27]([C:30]([F:33])([F:32])[F:31])=[N:28][N:29]=3)[N:26]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>N1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:18]1[CH2:17][CH2:16][N:15]([C:21]2[CH:22]=[CH:23][C:24]3[N:25]([C:27]([C:30]([F:31])([F:32])[F:33])=[N:28][N:29]=3)[N:26]=2)[CH2:20][CH2:19]1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 46681463HCID 46681463, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Naphthalene-2-sulfonyl chloride (175 mg, 0.77 mmol) was added to 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (150 mg, 0.55 mmol) in pyridine (2 mL). The resulting solution was stirred at room temperature for 18 hours. The reaction mixture was evaporated to remove the pyridine. The crude product was purified by preparative HPLC (Phenomenex Gemini C18 110A (axia) column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 6-[4-(naphthalen-2-ylsulfonyl)piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (168 mg, 66%) as a solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove the pyridine
  3. customThe crude product was purified by preparative HPLC (Phenomenex Gemini C18 110A (axia) column, 5μ silica, 19 mm diameter, 100 mm length)
  4. additionFractions containing the desired compound
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-90424f80cee54a4fa75d0cb7d1fea508
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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