Hydrochloric Acid → 5-((2H-1,2,3-Triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine

HRID 80642Notes

Reaction equation

HRID 80642 reaction equation
C(OC[N:9]1[CH:13]=[C:12]([CH2:14][O:15][C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH:26]=[N:25][N:24]=[N:23]3)=[CH:20][CH:21]=2)[N:11]=[N:10]1)(=O)C(C)(C)C.[OH-].[Na+].Cl>CO.C1COCC1.O>[N:9]1[NH:10][N:11]=[C:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[N:25][N:24]=[N:23]3)=[N:18][CH:17]=2)[CH:13]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57708433(4-((6-(1H-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Product 1

HCID 577083825-((2H-1,2,3-Triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-((6-(1H-tetrazol-1-yl)pyridin-3-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (10 g, 27.9 mmol) in MeOH (60 mL) and THF (6 mL) was added sodium hydroxide (61.5 mL of a 1M solution in water). The mixture was stirred for 30 minutes and hydrochloric acid was added (61.5 mL of a 1M solution in water). The resulting solution was extracted with ethyl acetate, separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford the expected product which was used in subsequent steps without further purification. 1H NMR (DMSO-d6): δ 10.07 (1H, s), 8.43-8.41 (2H, m), 8.00 (1H, d, J=8.8 Hz), 7.88 (1H, dd, J=3.2, 8.8 Hz), 6.32 (2H, s), 5.38 (2H, s), 1.08 (9H, s).

Workup

  1. extractionThe resulting solution was extracted with ethyl acetate
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-566f3e945c9b49caa96f6770fc64ab93
Source dataset
uspto-grants-2014_09
Patent number
US08846675B2

Reaction notes

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