Hydrochloric Acid → HCID 58382024, compound

HRID 1628076Notes

Reaction equation

HRID 1628076 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]3[C:12]([CH3:15])=[N:13][CH:14]=[C:9]3[CH:8]=[N:7][C:6]=2[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]2([CH3:35])OCC[O:31]2)=[CH:26][CH:25]=1)[CH3:2].Cl>CC(C)=O>[CH2:1]([C:3]1[C:11]2[N:10]3[C:12]([CH3:15])=[N:13][CH:14]=[C:9]3[CH:8]=[N:7][C:6]=2[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=1[C:24]1[CH:25]=[CH:26][C:27]([C:30](=[O:31])[CH3:35])=[CH:28][CH:29]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58382283HCID 58382283, compound

Product 1

HCID 58382024HCID 58382024, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8-Ethyl-1-methyl-7-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.147 g, 0.298 mmol, prepared using D from Preparation #5 with (E)-styreneboronic acid, E, F, G, I, J.2 with Ac2O and L.1 with mercury(II) trifluoracetate) was dissolved in acetone (10 mL) then HCl (5.0 N aqueous, 3.0 mL, 15 mmol) was added. The mixture was stirred at rt for about 1 h. The mixture was concentrated under reduced pressure then treated with saturated aqueous NaHCO3 (5 mL) and water (10 mL). The layers were separated then the aqueous mixture was extracted with DCM (25 mL then 2×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 1-(4-(8-ethyl-1-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-7-yl)phenyl)ethanone (0.092 g, 69%): LC/MS (Table 2, Method a) Rt=3.30 min; MS m/z 449 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthen treated with saturated aqueous NaHCO3 (5 mL) and water (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous mixture was extracted with DCM (25 mL
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06eb20ee08454fb8b265a11530562e86
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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