Azetidine → HCID 69093675, compound

HRID 2174276Notes

Reaction equation

HRID 2174276 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 was treated with a large excess of azetidine (˜30 eq). The resultant solution was warmed to 100° C. and stirred at that temperature for 18 h. The reaction solution was cooled to rt, poured into 1N NaOH solution and then extracted with EtOAc. The organic phases were dried over Na2SO4, filtered and conc. The crude product was purified using SiO2 chromatography and an appropriate gradient (MeOH—CH3CN (1:7)/CH2Cl2) to give 2-(5-(azetidin-1-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-3-yl)pyridine, I-23, as a white solid (88% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customconc. The crude product was purified

Sources & evidence

ORD record
ord-672c6b9fea084a2e8626cf73e7cf70cb
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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