tert-butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate → 1-(4-(dibenzylamino)-2-methylcyclopentyl)-2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)ethanone

HRID 1969849Notes

Reaction equation

HRID 1969849 reaction equation
[CH2:1]([N:8]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH:9]1[CH2:13][CH:12]([C:14](=[O:43])[CH2:15][N:16]([C:24]2[N:25]=[C:26]3[CH:32]=[CH:31][N:30]([S:33]([C:36]4[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=4)(=[O:35])=[O:34])[C:27]3=[N:28][CH:29]=2)C(=O)OC(C)(C)C)[CH:11]([CH3:44])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:45]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]1[CH2:13][CH:12]([C:14](=[O:43])[CH2:15][NH:16][C:24]2[N:25]=[C:26]3[CH:32]=[CH:31][N:30]([S:33]([C:36]4[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=4)(=[O:35])=[O:34])[C:27]3=[N:28][CH:29]=2)[CH:11]([CH3:44])[CH2:10]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

3

Reactant 1

HCID 58557498tert-butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate

Product 1

HCID 585570961-(4-(dibenzylamino)-2-methylcyclopentyl)-2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 2-(4-(dibenzylamino)-2-methylcyclopentyl)-2-oxoethyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)carbamate (6.19 g, 8.75 mmol) was dissolved in HCl (4 N in 1,4-dioxane, 25 mL). The reaction mixture was stirred at ambient temperature for about 2 h. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 and EtOAc (100 mL each). The organic phase was washed with brine (80 mL), dried over anhydrous MgSO4 and concd under reduced pressure to yield 1-(4-(dibenzylamino)-2-methylcyclopentyl)-2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)ethanone (5.2 g, 98%) as a brown amorphous solid: LC/MS (Table 1, Method a) Rt=3.00 min; MS m/z 608 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 and EtOAc (100 mL each)
  3. washThe organic phase was washed with brine (80 mL)
  4. dry with materialdried over anhydrous MgSO4 and concd under reduced pressure

Sources & evidence

ORD record
ord-b1cd1c66285542d79dd0c822550f6511
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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