1H-1,2,4-Triazole → HCID 10113408, compound

HRID 1357137Notes

Reaction equation

HRID 1357137 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[N:13]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25]>CN(C=O)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH:14]2[N:13]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)(=[O:25])=[O:26])[CH:12]([CH2:11][CH2:10][CH2:9][N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[CH2:16][CH2:15]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 22250442HCID 22250442, compound

Product 1

HCID 10113408HCID 10113408, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1,2,4-triazol (105 mg, 1.52 mmol) in DMF (15 ml) was added at 0° C. sodium hydride (61 mg, 1.52 mmol; 60%-disp.). The mixture was stirred at RT for 1 h, cooled to 0° C. and (2RS,5RS)-2-(3-chloro-propyl)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine (0.50 g, 1.26 mmol) was added. The reaction mixture was stirred at RT for 3 h and at 50° C. for 16 h, poured into ice/water (70 ml) and extracted with dichloromethane (2×100 ml). The combined organic layers were washed with water (70 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica gel (ethyl acetate) to yield the title compound (0.47 g, yield 87%) as a colorless oil, MS: m/e=429.5 (M+H+).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred at RT for 3 h and at 50° C. for 16 h
  3. extractionextracted with dichloromethane (2×100 ml)
  4. washThe combined organic layers were washed with water (70 ml) and brine (70 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-a07e82968a434a32b289867b8ec0ab5a
Source dataset
uspto-grants-2003_07
Patent number
US06589978B2

Reaction notes

Loading…