Sulfuric Acid → 8-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

HRID 1854388Notes

Reaction equation

HRID 1854388 reaction equation
OS(O)(=O)=O.[CH:6]1([C:12](=O)[CH2:13][N:14]([C:22]2[N:23]=[C:24]3[CH:30]=[CH:29][N:28]([S:31]([C:34]4[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=4)(=[O:33])=[O:32])[C:25]3=[N:26][CH:27]=2)C(=O)OC(C)(C)C)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>>[CH:6]1([C:12]2[N:23]3[C:24]4[CH:30]=[CH:29][N:28]([S:31]([C:34]5[CH:35]=[CH:36][C:37]([CH3:38])=[CH:39][CH:40]=5)(=[O:33])=[O:32])[C:25]=4[N:26]=[CH:27][C:22]3=[N:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 58010074tert-butyl 2-cyclohexyl-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate

Product 1

HCID 580098738-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

Procedure

Concentrated H2SO4 (4 mL) was added to tert-butyl 2-cyclohexyl-2-oxoethyl-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate (0.07 g, 0.14 mmol) and the reaction mixture was stirred for about 30 min at ambient temperature. The reaction mixture was poured onto ice-cold water (75 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine, dried over anhydrous MgSO4, and concentrated to yield 8-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine as a yellow oil that was used in Example #9, Step C without further purification (0.051 g, 95%): LC/MS (Table 2, Method a) Rt=2.79 min; MS m/z: 395 (M+H)+.

Workup

  1. additionThe reaction mixture was poured onto ice-cold water (75 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8efc50d013d24371a00baf3b3db7f16f
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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