Pyrrolidine → 2-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole

HRID 419339Notes

Reaction equation

HRID 419339 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCOCC1>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([C:5]2[O:4][C:3]([CH2:2][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:7][N:6]=2)[CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 594526612-(Chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole

Product 1

HCID 594529402-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazoleYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2-(chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole (Example 26, step C) (1.01 g, 3.75 mmol) in dioxane (10 mL) was added pyrrolidine (0.800 mL, 9.58 mmol). The reaction was stirred at rt overnight. Upon completion by TLC, the reaction mixture was treated with BOC-anhydride (0.371 g, 1.69 mmol) and cooled to 0° C. The mixture was treated with TEA (0.279 mL, 2.00 mmol). Purification by flash chromatography provided the title compound of step A (1.13 g, 3.70 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.72 (m, 4H), 2.56 (br. s., 4H), 3.92-3.96 (m, 2H), 3.98-4.02 (m, 3H), 7.64-7.69 (m, 1H), 7.79 (br. s., 1H), 8.01-8.06 (m, 1H).

Workup

  1. temperaturecooled to 0° C
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-5d323fd7674d46148f536f01b15bd23c
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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