Azetidine → HCID 69093675, compound

HRID 2174267Notes

Reaction equation

HRID 2174267 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:3]=1.[NH:21]1[CH2:24][CH2:23][CH2:22]1.[OH-].[Na+]>CC(N(C)C)=O>[N:21]1([C:2]2[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[F:14])[N:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[N:3]=2)[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 14798Sodium HydroxideHCID 69094001HCID 69094001, compound

Product 1

HCID 69093675HCID 69093675, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-(5-bromo-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-16), in DMA is treated with a large excess of azetidine (e.g., ˜30 eq). The resultant solution is warmed to about 100° C. and stirred at that temperature for about 18 h. The reaction solution is cooled to room temperature, poured into 1N NaOH solution and then extracted with EtOAc. The organic phases are dried, e.g., over MgSO4 or Na2SO4, filtered and concentrated. The crude product is purified using SiO2 chromatography and an appropriate gradient (MeOH—CH3CN (1:7)/CH2Cl2) to yield 2-(5-(azetidin-1-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine (I-23) as a solid.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phases are dried
  3. filtratione.g., over MgSO4 or Na2SO4, filtered
  4. concentrationconcentrated
  5. customThe crude product is purified

Sources & evidence

ORD record
ord-e719f5bef96b4b0fac7973db14d54381
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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