Formic Acid → HCID 90410090, compound

HRID 2177633Notes

Reaction equation

HRID 2177633 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]=[N:9][N:10]([C:11]3[CH:16]=[N:15][CH:14]=[CH:13][N:12]=3)[C:4]=2[CH:3]=1.C(O)=O.C(N(CC)CC)C.[OH-].[Na+]>>[CH3:1][CH:2]1[NH:7][CH2:6][C:5]2[N:8]=[N:9][N:10]([C:11]3[CH:16]=[N:15][CH:14]=[CH:13][N:12]=3)[C:4]=2[CH2:3]1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 90409506HCID 90409506, compound

Product 1

HCID 90410090HCID 90410090, compound

Conditions

Temperature
140 °C

Procedure

To a solution of 6-methyl-1-(pyrazin-2-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine (245 mg, 1.15 mmol) in formic acid (0.70 mL, 18.5 mmol) was added dropwise triethylamine (1.28 mL, 9.24 mmol). The resulting mixture was heated to 140° C. for 24 h. The reaction was cooled and 1M NaOH was added until the pH was 7-9. The water layer was extracted with CH2Cl2 three times. The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated. The residue was dissolved in 3:1 isopropanol/concentrated HCl (4 mL) and stirred at 50° C. for 16 h. The reaction was cooled and 1M NaOH was added until pH 12 was reached. The water layer was extracted with 1:4 isopropanol/CH2Cl2 three times. The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated to a yellow solid (230 mg, 92%). MS (ESI) mass calcd. C10H12N6, 216.11. m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 9.51-9.47 (m, 1H), 8.64-8.60 (m, 1H), 8.49-8.46 (m, 1H), 4.26-4.08 (m, 2H), 3.37-3.28 (m, 1H), 3.14-3.04 (m, 1H), 2.85-2.74 (m, 1H), 2.23-2.02 (br s, 1H), 1.36 (d, J=6.3 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe water layer was extracted with CH2Cl2 three times
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 3:1 isopropanol/concentrated HCl (4 mL)
  7. temperatureThe reaction was cooled
  8. addition1M NaOH was added until pH 12
  9. extractionThe water layer was extracted with 1:4 isopropanol/CH2Cl2 three times
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated to a yellow solid (230 mg, 92%)

Sources & evidence

ORD record
ord-30fc319795df4749836e0ea324e60051
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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