Trifluoroacetic acid → HCID 44200331, compound

HRID 600388Notes

Reaction equation

HRID 600388 reaction equation
[CH:1]1([N:6]([CH3:30])[C:7]2[N:8]=[C:9]3[C:15]([C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:14][N:13](COCC[Si](C)(C)C)[C:10]3=[N:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.O.O.O.C([O-])(=O)C.[Na+]>ClCCl>[CH:1]1([N:6]([CH3:30])[C:7]2[N:8]=[C:9]3[C:15]([C:16](=[O:21])[C:17]([CH3:18])([CH3:20])[CH3:19])=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23665404Sodium Acetate TrihydrateHCID 57831045HCID 57831045, compound

Product 1

HCID 44200331HCID 44200331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of impure 1-[2-(cyclopentyl-methyl-amino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one, prepared according to general procedures as described in these Examples, (0.030 g, 0.071 mmol) in 1 mL of dichloromethane and 1 mL of trifluoroacetic acid was stirred for 3 h, then concentrated, chasing with toluene, to a yellow oil. The oil was dissolved in 1 mL of ethanol and treated with sodium acetate trihydrate (0.103 g, 0.760 mmol). The yellow mixture was stirred for 16 h, then concentrated to a yellow solid. Column chromatography (two columns: first run, 0→40% EtOAc/hexanes; second run, 66% ether/hexanes) afforded 0.0045 g (21% from impure, 12% two-step) of 1-[2-(cyclopentyl-methyl-amino)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe oil was dissolved in 1 mL of ethanol
  3. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-0e5851c8a0d644d98a2ee5d180d55c73
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

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