Ethyl orthoformate → HCID 77230636, compound

HRID 2173413Notes

Reaction equation

HRID 2173413 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH:5](OCC)(OCC)OCC.[CH3:15][C:16]1[CH:21]=[C:20]([NH2:22])[N:19]=[CH:18][C:17]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)(=O)C.O>[CH3:15][C:16]1[CH:21]=[C:20]([N:22]2[CH:5]=[N:3][N:2]=[N:1]2)[N:19]=[CH:18][C:17]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 77230637HCID 77230637, compound

Product 1

HCID 77230636HCID 77230636, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide (0.712 g, 11.0 mmol) was added to a stirred mixture of triethyl orthoformate (1.95 ml, 11.7 mmol) and ethyl (4-methyl-6-aminopyridin-3-yl)acetate (1.42 g, 7.30 mmol) in acetic acid (10 ml) and the mixture was stirred at 80° C. for 24 h. The reaction mixture was cooled, diluted with water, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated to provide ethyl [4-methyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.57 (s, 1H), 8.35 (s, 1H), 7.98 (s, 1H), 4.23 (m, 2H), 3.78 (s, 2H), 2.71 (s, 3H), 1.27 (m, 3H). LC-MS (IE, m/z): 248 [M+1]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-034d8d0876fe4774812dfd58a55acd59
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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