p-Toluenesulfonic acid → HCID 178439992, compound

HRID 923336Notes

Reaction equation

HRID 923336 reaction equation
[CH:1]([C:4]1[N:8]=[C:7]([NH2:9])[NH:6][N:5]=1)([CH3:3])[CH3:2].[NH:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19](=O)[CH2:20][C:21](OCC)=[O:22])=[CH:18][C:13]=2[N:12]=[N:11]1.CC1C=CC(S(O)(=O)=O)=CC=1>CCCCO>[NH:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[NH:9][C:7]4[N:6]([N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:8]=4)[C:21](=[O:22])[CH:20]=3)=[CH:18][C:13]=2[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 178440450HCID 178440450, compoundHCID 178472159HCID 178472159, compound

Product 1

HCID 178439992HCID 178439992, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-isopropyl-1H-1,2,4-triazol-5-amine (100 mg, 0.79 mmol) in n-BuOH (1 mL) was added ethyl 3-(1H-benzo[d][1,2,3]triazol-5-yl)-3-oxopropanoate (275 mg, 1.18 mmol) and TsOH (7 mg, 0.04 mmol), and the resulting mixture was stirred for 5 h at 130° C. The solids were collected by filtration and washed with MeOH (3×1 mL) to afford 5-(1H-benzo[d][1,2,3]triazol-5-yl)-2-isopropyl-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a off-white solid (45 mg, 19%).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with MeOH (3×1 mL)

Sources & evidence

ORD record
ord-53c0b9fe94fc414e89835872137e6a7e
Source dataset
uspto-grants-2016_03
Patent number
US09278973B2

Reaction notes

Loading…