Hydrochloric Acid → HCID 58382074, compound

HRID 1628042Notes

Reaction equation

HRID 1628042 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[N:7][C:6]=2[N:5](COCC[Si](C)(C)C)[C:4]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29]2([CH3:34])OCC[O:30]2)=[CH:25][CH:24]=1)[CH3:2].Cl.C(O)(C(F)(F)F)=O.[NH4+].[OH-]>CC(C)=O.C(Cl)Cl>[CH2:1]([C:3]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH:8]=[N:7][C:6]=2[NH:5][C:4]=1[C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:30])[CH3:34])=[CH:25][CH:24]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 58382163HCID 58382163, compound

Product 1

HCID 58382074HCID 58382074, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-2-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-dipyrrolo[1,2-a:2′,3′-e]pyrazine (0.194 g, 0.406 mmol) was dissolved in acetone (6 mL) then treated with concentrated aqueous HCl (36 wt %, 0.170 mL, 2.08 mmol). The mixture was stirred at rt for 30 min. The solvents were evaporated under reduced pressure and then the material was treated with DCM (3 mL) and TFA (1.5 mL, 19 mmol). The mixture was stirred at rt for about 15 min then the solvents were evaporated under reduced pressure. The residue was dissolved in 1,4-dioxane (4 mL) then treated with concentrated aqueous NH4OH (26 wt %, 2 mL, 13.87 mmol). The mixture was stirred at rt for 30 min then warmed to about 50° C. for about 15 min. The mixture was cooled to rt and the solvents removed under reduced pressure. The material was treated with water (15 mL) then stirred for about 5 min at rt. The solids were collected by filtration then dried under vacuum at about 60° C. to a constant weight to give 1-(4-(1-ethyl-3H-dipyrrolo[1,2-a:2′,3′-e]pyrazin-2-yl)phenyl)ethanone (0.074 g, 60%): LC/MS (Table 2, Method b) Rt=2.37 min; MS m/z 304 (M+H)+.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. stirringThe mixture was stirred at rt for about 15 min
  3. customthe solvents were evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 1,4-dioxane (4 mL)
  5. stirringThe mixture was stirred at rt for 30 min
  6. temperaturethen warmed to about 50° C. for about 15 min
  7. temperatureThe mixture was cooled to rt
  8. customthe solvents removed under reduced pressure
  9. additionThe material was treated with water (15 mL)
  10. stirringthen stirred for about 5 min at rt
  11. filtrationThe solids were collected by filtration
  12. customthen dried under vacuum at about 60° C. to a constant weight

Sources & evidence

ORD record
ord-1f9ec83d09c6454691102382b749fcc5
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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