Ammonium Chloride → 7-(2H-Tetrazol-5-yl)-imidazo[1,2-a]pyridine

HRID 1894188Notes

Reaction equation

HRID 1894188 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[NH4+].[Cl-].[N:7]1[CH:8]=[CH:9][N:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=12>CN(C=O)C.CCOCC>[N:1]1[NH:2][N:3]=[N:17][C:16]=1[C:13]1[CH:14]=[CH:15][N:10]2[CH:9]=[CH:8][N:7]=[C:11]2[CH:12]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 55267408Imidazo(1,2-a)pyridine-7-carbonitrile

Product 1

HCID 592777617-(2H-Tetrazol-5-yl)-imidazo[1,2-a]pyridineYield 330%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide (97 mg, 1.45 mmol) was added to a stirred mixture of NH4Cl (82 mg, 1.53 mmol) and imidazo[1,2-a]pyridine-7-carbonitrile (200 mg, 1.4 mmol) in dry DMF (5 ml) at RT under N2. The reaction was stirred and heated at 80° C. in a sealed vial for 10 hours. [3 identical reactions were run in parallel] After cooling to RT the reaction mixtures were combined and diluted with Et2O. The solid was collected by filtration and dried to give the title compound (860 mg) as a light brown solid. [presumably contains NaCl] 1H NMR (400 MHz, DMSO-d6): 8.55 (1H, dd), 8.02 (1H, s), 7.94 (1H, s), 7.57 (1H, d), 7.54 (1H, dd).

Workup

  1. temperature[3 identical reactions were run in parallel] After cooling to RT
  2. customthe reaction mixtures
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-e9df32d84e2441c2bb357f0c68b8f5a7
Source dataset
uspto-grants-2013_08
Patent number
US08513276B2

Reaction notes

Loading…