Pyrrolidine → 2,2-dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]3[C:16]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>CN1CCCC1=O>[CH3:19][C:18]([CH3:21])([CH3:20])[C:17]([C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[CH:7]=3)[N:9]=2)[NH:14][CH:15]=1)=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 1-[2-(2-chloro-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.030 g, 0.095 mmol), 0.100 mL of pyrrolidine and 1.5 mL of N-methylpyrollidinone was stirred at 150° C. in a pressure tube for 3 h. The resulting black solution was partitioned between 30 mL of ethyl acetate and 40 mL of water. The organic layer was washed with three 30 mL portions of water, dried over MgSO4, filtered and concentrated to a residue. Silica gel chromatography (0->60% EtOAc/hexanes) afforded 0.020 g (61%) of 2,2-dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a yellow solid.
Workup
- customThe resulting black solution was partitioned between 30 mL of ethyl acetate and 40 mL of water
- washThe organic layer was washed with three 30 mL portions of water
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to a residue
Sources & evidence
- ORD record
- ord-a00e669d48164cc889af15a90500f0cf
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939531B2
Reaction notes
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