Methanol → 5-[3-(2-Fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-1,3,4-oxadiazol-2(3H)-one

HRID 1875458Notes

Reaction equation

HRID 1875458 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]([NH:16][NH2:17])=[O:15])[N:6]=1.[CH3:22][OH:23]>>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]2[O:15][C:22](=[O:23])[NH:17][N:16]=2)[N:6]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 591778763-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carbohydrazide

Product 1

HCID 247944285-[3-(2-Fluorobenzyl)imidazo[1,5-a]pyridin-1-yl]-1,3,4-oxadiazol-2(3H)-one

Procedure

155 mg (0.55 mmol) of 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carbohydrazide from example 16A are dissolved in 3 ml of methanol. 106 mg (0.65 mmol) of N,N′-carbonyldiimidazole are added, and the mixture is heated to reflux for 2 h. It is then purified directly by preparative HPLC to result in 98 mg (58% of theory) of the desired compound as a pale beige solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 2 h
  3. customIt is then purified directly by preparative HPLC

Sources & evidence

ORD record
ord-4a5d8a3501a04125bf9ea27be4261eb9
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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