Sodium Bicarbonate → HCID 86660660, compound

HRID 659152Notes

Reaction equation

HRID 659152 reaction equation
C[O:2][CH:3](OC)[C:4]1[NH:5][C:6]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)=[C:7]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([N:15]=[CH:16][N:17]=3)[CH:14]=2)[N:8]=1.C([O-])(O)=O.[Na+]>Cl>[N:17]1[CH:16]=[N:15][N:13]2[CH:14]=[C:9]([C:7]3[N:8]=[C:4]([CH:3]=[O:2])[NH:5][C:6]=3[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=3)[CH:10]=[CH:11][C:12]=12

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66632546HCID 66632546, compound

Product 1

HCID 86660660HCID 86660660, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

6-(2-(Dimethoxymethyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine (6.00 g, 17.12 mmol) was dissolved in 1 N HCl (120 mL), and the mixture was heated at 70° C. for 3 h. The reaction mixture was allowed to cool to 0° C., and then it was neutralized with saturated aqueous NaHCO3 solution. The mixture was extracted with 10% MeOH in CHCl3 (3×200 mL), and the organic phase was dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure to give the titled compound (4.69 g, 90%) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 9.82 (s, 1H), 9.01 (br s, 1H), 8.41 (s, 1H), 7.85 (dd, 1H, J=9.2, 0.8 Hz), 7.82 (dd, 1H, J=9.2, 1.6 Hz), 7.55 (t, 1H, J=7.8 Hz), 7.33 (br s, 1H), 7.16 (d, 1H, J=8.0 Hz), 2.60 (s, 3H).

Workup

  1. temperatureto cool to 0° C.
  2. extractionThe mixture was extracted with 10% MeOH in CHCl3 (3×200 mL)
  3. dry with materialthe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-caeef44e9e6847bfbd8eef4b661dcc0b
Source dataset
uspto-grants-2011_12
Patent number
US08080568B1

Reaction notes

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