1H-1,2,4-Triazole → HCID 86679114, compound

HRID 1774730Notes

Reaction equation

HRID 1774730 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[CH2:20]Cl)[CH:14]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[CH2:20][N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)[CH:14]=1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 86679113HCID 86679113, compound

Product 1

HCID 86679114HCID 86679114, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of NaH (0.011 g, 0.272 mmol) in DMF (1 mL) was added 1H-1,2,4-triazole (0.016 g, 0.236 mmol) and the reaction mixture was stirred at room temperature for 30 min. Then, 3-bromo-5-((S)-2-chloromethyl-pyrrolidin-1-yl)-pyridine (0.05 g, 0.181 mmol) in DMF (0.5 mL) was added to the reaction mixture which was heated to 80° C. over night. The mixture was diluted with DCM, poured into aq. NaHCO3 (5 mL) and the aqueous layer was extracted with DCM (2×10 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.04 g, 72%) as a yellow oil. MS: 308.0, 310.0 (M+H+).

Workup

  1. temperaturewas heated to 80° C. over night
  2. extractionthe aqueous layer was extracted with DCM (2×10 mL)
  3. dry with materialCombined organics were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-582f91338de142bab6c18734bb6d132d
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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