Benzyl Bromide → HCID 58558319, compound

HRID 82710Notes

Reaction equation

HRID 82710 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10](=[O:19])[O:9][N:8]=2)=[N:4][O:5][N:6]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:12]([N:11]1[C:10](=[O:19])[O:9][N:8]=[C:7]1[C:3]1[C:2]([NH:1][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:6][O:5][N:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 7498Benzyl Bromide2×HCID 674354223-(4-amino-1,2,5-oxadiazol-3-yl)-4-benzyl-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 58558319HCID 58558319, compoundYield 15%

Procedure

A solution of 3-(4-amino-1,2,5-oxadiazol-3-yl)-4-benzyl-1,2,4-oxadiazol-5(4H)-one (60.0 mg, 0.231 mmol) and benzyl bromide (28 μL, 0.23 mmol) was heated at 150° C. for 5 h. Additional benzyl bromide (28 μL) was added to the incomplete reaction and heating was continued for another 16 h. Purification of the crude reaction mixture by preparative HPLC gave the desired product (12 mg, 15%). LCMS for C18H16N5O3 (M+H)+: m/z=349.9.

Workup

  1. temperatureheating
  2. customPurification of the crude
  3. customreaction mixture by preparative HPLC

Sources & evidence

ORD record
ord-5f68e3df14e94b63a37cbb13c1c489c4
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

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