Sodium hydride → HCID 86701050, compound

HRID 715738Notes

Reaction equation

HRID 715738 reaction equation
[H-].[Na+].[OH:3][CH:4]([CH2:10][CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[N:20][N:21]=2)[N:18]=1>CN(C=O)C>[S:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:19]1[N:17]2[N:18]=[C:13]([O:3][CH:4]([CH2:10][CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:14]=[CH:15][C:16]2=[N:21][N:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 521365Ethyl 2-HydroxybutyrateHCID 431444026-Chloro-3-(thiophen-2-yl)[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 86701050HCID 86701050, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (1.5 equiv., 60% in mineral oil) was added at 0° C. to a solution of ethyl 2-hydroxybutyrate (1.5 equiv.) in dry DMF (7 mL) under argon atmosphere and the mixture was stirred for 10 min. To this mixture was added 6-chloro-3-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine (1 mmol) dissolved in DMF (3 mL). After 30 min, TLC showed that all the staring material was consumed. The solution was extracted with ethyl acetate, washed with water twice and concentrated. The crude syrup thus obtained was purified by flash column chromatography to give ethyl 2-((3-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)oxy)butanoate.

Workup

  1. waitAfter 30 min
  2. customwas consumed
  3. extractionThe solution was extracted with ethyl acetate
  4. washwashed with water twice
  5. concentrationconcentrated
  6. customThe crude syrup thus obtained
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-75c2593373434ac780b948d4ce341010
Source dataset
uspto-grants-2015_11
Patent number
US09187484B2

Reaction notes

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