(Diethylamino)sulfur trifluoride → HCID 59149784, compound

HRID 1675069Notes

Reaction equation

HRID 1675069 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]([F:33])([F:32])[C:12]1[N:16]2[N:17]=[C:18]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][O:28][CH2:29][CH2:30]O)[CH2:23][CH2:22]3)[CH:19]=[CH:20][C:15]2=[N:14][N:13]=1>C(Cl)Cl>[F:7][CH2:30][CH2:29][O:28][CH2:27][CH:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:19]=[CH:20][C:15]3[N:16]([C:12]([C:11]([F:33])([F:32])[F:10])=[N:13][N:14]=3)[N:17]=2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67340712HCID 67340712, compound

Product 1

HCID 59149784HCID 59149784, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Diethylamino)sulfur trifluoride (0.059 mL, 0.45 mmol) was added dropwise to a stirred solution of 2-[[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl)methoxy]ethanol (104 mg, 0.3 mmol) in DCM (3 mL) at −70° C. The solution was allowed to warm to ambient temperature and stir for 18 hours. The solution was diluted with DCM and washed with 2M aqueous K2CO3. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD 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-[(2-fluoroethoxy)methyl]piperidin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (22.0 mg, 21%) as a white solid.

Workup

  1. washwashed with 2M aqueous K2CO3
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customThe crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  5. additionFractions containing the desired compound
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-a1b3681539854ce49b6fb10a3f2f0f52
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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