3-Fluorophenol → HCID 59149724, compound

HRID 1675064Notes

Reaction equation

HRID 1675064 reaction equation
CS([O:5][CH:6]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]([F:22])([F:21])[F:20])=[N:17][N:18]=3)[N:15]=2)[CH2:7]1)(=O)=O.[F:23][C:24]1[CH:25]=[C:26](O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.CC#N>[F:23][C:24]1[CH:29]=[C:28]([CH:27]=[CH:26][CH:25]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([C:19]([F:22])([F:21])[F:20])=[N:17][N:18]=3)[N:15]=2)[CH2:7]1

Participants

7

Reactant 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 86638079HCID 86638079, compound

Product 1

HCID 59149724HCID 59149724, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred partial solution of 6-[3-(methanesulfonyloxy)azetidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (169 mg, 0.5 mmol), 3-fluorophenol (112 mg, 1.5 mmol) and potassium carbonate (207 mg, 1.5 mmol) in DMF (3 mL) was heated at 100° C. for 24 hours. The reaction mixture was filtered and the product was isolated 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 give 6-[3-(3-fluorophenoxy)azetidin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (58 mg, 33%) as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe product was isolated by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)

Sources & evidence

ORD record
ord-be68590b58364027a35b2a8c5bab06db
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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