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Hydrochloric Acid → N-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide

HRID 1854402
Notes
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Reaction equation

HRID 1854402 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C:23]45[CH2:30][CH2:29][C:26]([NH:31]C(=O)OC(C)(C)C)([CH2:27][CH2:28]4)[CH2:25][CH2:24]5)=[N:21][CH:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl.[CH:40]1([S:43](Cl)(=[O:45])=[O:44])[CH2:42][CH2:41]1>CN(C=O)C>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C:23]45[CH2:28][CH2:27][C:26]([NH:31][S:43]([CH:40]6[CH2:42][CH2:41]6)(=[O:45])=[O:44])([CH2:29][CH2:30]4)[CH2:25][CH2:24]5)=[N:21][CH:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2760919Cyclopropanesulfonyl chlorideHCID 58009897tert-butyl 4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-ylcarbamate

Product 1

HCID 58010073N-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamideYield 14.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a flask containing tert-butyl 4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-ylcarbamate (0.175 g, 0.327 mmol) was added a solution of HCl (4 N in 1,4-dioxane, 5 mL). After about 2 h at ambient temperature, the reaction mixture was concentrated under reduced pressure. The crude amine hydrochloride was dissolved in DCM (10 mL) and TEA (0.36 mL, 2.6 mmol) was added to the reaction mixture followed by cyclopropanesulfonyl chloride (0.18 g, 1.3 mmol). After about 2 h at ambient temperature, DMF (3 mL) was added and the reaction mixture was concentrated under reduced pressure to remove DCM. After a further about 4 h at ambient temperature, EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL) was added to the reaction mixture. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude reaction mixture was purified by chromatography on silica gel using 20-80% EtOAc in DCM to provide N-(4-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide as a tan solid (0.025 g, 14%). LC/MS (Table 2, Method a) Rt=2.34 min; MS m/z: 540 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe crude amine hydrochloride was dissolved in DCM (10 mL)
  3. waitAfter about 2 h at ambient temperature
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customto remove DCM
  6. waitAfter a further about 4 h at ambient temperature
  7. additionEtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL) was added to the reaction mixture
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude reaction mixture
  13. customwas purified by chromatography on silica gel using 20-80% EtOAc in DCM

Sources & evidence

ORD record
ord-61c76a7917b94f1796bdb1a0f48dea35
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08962629B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes