Hydrochloric Acid → 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone

HRID 1969552Notes

Reaction equation

HRID 1969552 reaction equation
[CH2:1]([C@@H:3]1[CH2:11][C:6]2(OCC[O:7]2)[CH2:5][C@@H:4]1[C:12]1[N:16]2[C:17]3[CH:23]=[CH:22][N:21]([S:24]([C:27]4[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[C:18]=3[N:19]=[CH:20][C:15]2=[N:14][N:13]=1)[CH3:2].Cl>C1COCC1>[CH2:1]([CH:3]1[CH:4]([C:12]2[N:16]3[C:17]4[CH:23]=[CH:22][N:21]([S:24]([C:27]5[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=5)(=[O:26])=[O:25])[C:18]=4[N:19]=[CH:20][C:15]3=[N:14][N:13]=2)[CH2:5][C:6](=[O:7])[CH2:11]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 679986721-((7S,8R)-8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 585571653-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanoneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with 1-((7S,8R)-8-ethyl-1,4-dioxaspiro[4.4]nonan-7-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (3.56 g, 7.61 mmol) and THF (20 mL). To the solution was added aqueous HCl (6N, 3.81 mL, 22.8 mmol) and the mixture was stirred at rt for about 2 h. The solvent was removed under reduced pressure and DCM (75 mL) and water (50 mL) were added. The layers were separated and the organic solution was dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone as a brown foam (2.99 g, 93%): LC/MS (Table 1, Method c) Rt=1.40 min; MS m/z: 424 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure and DCM (75 mL) and water (50 mL)
  2. additionwere added
  3. customThe layers were separated
  4. dry with materialthe organic solution was dried over anhydrous MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a1957f0e68f9411ca09f8f2fa9a9dcc0
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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