Triethylamine → HCID 86638076, compound

HRID 1675000Notes

Reaction equation

HRID 1675000 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:26])([F:25])[C:8]1[N:12]2[N:13]=[C:14]([N:17]3[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]3)[CH:15]=[CH:16][C:11]2=[N:10][N:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:24][CH2:23][CH:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:15]=[CH:16][C:11]3[N:12]([C:8]([C:7]([F:6])([F:25])[F:26])=[N:9][N:10]=3)[N:13]=2)[CH2:18][CH2:19]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 60504383HCID 60504383, compound

Product 1

HCID 86638076HCID 86638076, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (2.83 mL, 36.51 mmol) in DCM (30 mL) was added dropwise to a stirred partial solution of [1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]methanol (10 g, 33.19 mmol) and triethylamine (5.09 mL, 36.51 mmol) in DCM (140 mL). The reaction was stirred for 20 minutes, quenched with water (100 mL) and extracted with DCM (2×75 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford a yellow solid. The crude solid was triturated with ether to give a solid which was collected by filtration and dried under vacuum to give 6-[4-(methanesulfonyloxymethyl)piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (7.60 g, 60.4%) as a white solid.

Workup

  1. customquenched with water (100 mL)
  2. extractionextracted with DCM (2×75 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a yellow solid
  7. customThe crude solid was triturated with ether
  8. customto give a solid which
  9. filtrationwas collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-cb15fa050fc8473eade2e371d0fec0fe
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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