Hydrochloric Acid → 3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine

HRID 253952Notes

Reaction equation

HRID 253952 reaction equation
C([NH:5][C:6]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=3[F:24])[N:15]=[N:14][N:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)(C)(C)C.Cl.[OH-].[Na+]>CO>[F:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[N:16]1[C:12]([C:11]2[C:6]([NH2:5])=[N:7][CH:8]=[CH:9][CH:10]=2)=[N:13][N:14]=[N:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58179708N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine

Product 1

HCID 581800123-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine was dissolved in MeOH (10 mL), treated with 6N HCl (20 mL), and heated to reflux for 2 hours. The mixture was subsequently cooled to RT and neutralized with 6N NaOH. The resulting precipitate was collected, washed with water, and dried in vacuo to give 3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine as white solid. Using the same procedure, 3-(1-(2,3-dichlorophenyl)-H-tetrazol-5-yl)pyridin-2-amine and 3-(1-(3-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine can be produced from N-tert-butyl-3-(1-(2,3-dichlorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine and N-tert-butyl-3-(1-(3-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine, respectively.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-45653e8ae3b3424abcc495588eb724c2
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

Loading…