Sodium Acetate Trihydrate → 1-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

HRID 600397Notes

Reaction equation

HRID 600397 reaction equation
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:18][N:17](COCC[Si](C)(C)C)[C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.O.C([O-])(=O)C.[Na+]>ClCCl.FC(F)(F)C(O)=O>[CH:1]1([NH:7][C:8]([NH:10][C:11]2[N:12]=[C:13]3[C:19]([C:20](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 23665404Sodium Acetate TrihydrateHCID 578310441-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea

Product 1

HCID 442003261-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureaYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (0.102 g, 0.215 mmol) in 2 mL of dichloromethane and 2 mL of trifluoroacetic acid was stirred for 1 h, then concentrated, chasing twice with toluene. The residue was dissolved in 2 mL of ethanol and treated with sodium acetate trihydrate (0.293 g, 2.15 mmol). The mixture was stirred for 16 h, then concentrated to a residue. Column chromatography (50→80% EtOAc/hexanes) afforded 0.050 g (68%) of 1-cyclohexyl-3-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 2 mL of ethanol
  3. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-866b9559e0c84c84b9504f3036b17eca
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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