Sodium Acetate Trihydrate → HCID 59540731, compound

HRID 1677518Notes

Reaction equation

HRID 1677518 reaction equation
[CH3:1][C:2]([CH3:42])([CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:12]=2)[N:7](COCC[Si](C)(C)C)[CH:6]=1)=[O:4].O.O.O.C([O-])(=O)C.[Na+]>ClCCl.FC(F)(F)C(O)=O>[CH3:1][C:2]([CH3:42])([CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 23665404Sodium Acetate TrihydrateHCID 59540935HCID 59540935, compound

Product 1

HCID 59540731HCID 59540731, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2,2-dimethyl-4-morpholin-4-yl-1-[2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butan-1-one (0.024 g, 0.040 mmol) in 1 mL of dichloromethane and 0.5 mL of trifluoroacetic acid was stirred for 3 h, then concentrated. The resulting residue was dissolved in 1 mL of ethanol and treated with sodium acetate trihydrate (0.054 g, 0.40 mmol). The mixture was stirred for 16 h, then concentrated to a residue. Column chromatography (0→10% MeOH/CH2Cl2) afforded 0.014 g (75%) of 2,2-dimethyl-4-morpholin-4-yl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butan-1-one as a brown solid.

Workup

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

Sources & evidence

ORD record
ord-252c5e8d42e440bc83c35bf871fb284b
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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