Triethylamine → HCID 86638079, compound

HRID 1675066Notes

Reaction equation

HRID 1675066 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:23])([F:22])[C:8]1[N:12]2[N:13]=[C:14]([N:17]3[CH2:20][CH:19]([OH:21])[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:21][CH:19]1[CH2:20][N:17]([C:14]2[CH:15]=[CH:16][C:11]3[N:12]([C:8]([C:7]([F:6])([F:22])[F:23])=[N:9][N:10]=3)[N:13]=2)[CH2:18]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67339947HCID 67339947, compound

Product 1

HCID 86638079HCID 86638079, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.929 mL, 12 mmol) was added dropwise to a stirred partial solution of 1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)azetidin-3-ol (2.59 g, 10 mmol) and triethylamine (1.951 mL, 14 mmol) in DCM (17 mL) at 0° C. The solution was allowed to warm to ambient temperature and stirred for 30 minutes. The precipitate was collected by filtration, washed with a little DCM, a little ethanol and ether. It was dried under vacuum to afford 6-[3-(methanesulfonyloxy)azetidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (2.400 g, 71.2%) as a white crystalline solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with a little DCM
  3. customIt was dried under vacuum

Sources & evidence

ORD record
ord-5dc118bf11b64d3699241fa553a4212c
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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