Hydrochloric Acid → HCID 86687900, compound

HRID 868990Notes

Reaction equation

HRID 868990 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[N:7]([CH3:19])[CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17]C)=[N:15][CH:16]=2)[N:10]=1.C(Cl)Cl.Cl.C(=O)(O)[O-].[Na+]>CC#N>[CH3:19][N:7]1[CH:8]=[C:9]([C:11]2[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:10]=[C:6]1[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 70096051HCID 70096051, compound

Product 1

HCID 86687900HCID 86687900, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 5-(2-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-4-yl)-2-ethylpyridine (140 mg, 0.571 mmol), DCM (5 mL), and 4 N HCl (5 mL) was heated to 45° C. for 16 h. Then the mixture was cooled to room temperature, the pH was adjusted to 6 with saturated sodium bicarbonate solution at 0° C., and the mixture was concentrated to give a crude product. 30 mL of CH3CN was added and the mixture was filtered. The filtrate was then concentrated to afford a white solid (90 mg). MS (ESI): m/z 202.1 [M+H]+.

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. customto give a crude product
  4. filtrationthe mixture was filtered
  5. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-17ba79a7524745bf999191892fefe34f
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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