Potassium Carbonate → Methyl 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]acetate

HRID 1675167Notes

Reaction equation

HRID 1675167 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([OH:33])[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[CH:22][C:23]4[N:24]([C:26]([C:29]([F:32])([F:31])[F:30])=[N:27][N:28]=4)[N:25]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:33][C:14]1([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=2)[CH2:15][CH2:16][N:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:24]([C:26]([C:29]([F:32])([F:31])[F:30])=[N:27][N:28]=3)[N:25]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 667887034-(4-Hydroxyphenyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

Product 1

HCID 67340075Methyl 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]acetateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-bromoacetate (0.121 mL, 1.28 mmol) was added to 4-(4-hydroxyphenyl)-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (323 mg, 0.85 mmol) and potassium carbonate (235 mg, 1.70 mmol) in DMF (5 mL). The resulting suspension was stirred at ambient temperature for 16 hours. The reaction mixture was evaporated to dryness, then water (50 mL) was added and the mixture was stirred for 20 minutes. The resulting precipitate was collected by filtration, washed with water then ether and dried to afford methyl 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]acetate (384 mg, 100%) as a beige solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionwater (50 mL) was added
  3. stirringthe mixture was stirred for 20 minutes
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialether and dried

Sources & evidence

ORD record
ord-972e1c9be7ab4ffea26d17dca33f1351
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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