3-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-N,N-diethylprop-2-yn-1-amine → 3-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-N,N-diethylpropan-1-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([C:22]#[C:23][CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>CO.[Pd]>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[NH:19][C:16]3=[N:17][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 3-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-N,N-diethylprop-2-yn-1-amine (from Example 27, 5 mg, 12.7 μmol) in methanol (2 mL), Pd/C (10% w/w, 5.0 mg, 4.7 μmol) was added. The resulted mixture was stirred under H2 at ambient temperature. After 1.5 hours, the palladium catalyst was filtered and the crude mixture was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min) to give the desired product (2.4 mg, 50%) as its TFA salt. LCMS calculated for C23H33N4O2 (M+H)+: m/z=397.3. Found: 397.3.
Workup
- filtrationthe palladium catalyst was filtered
- customthe crude mixture was purified on RP-HPLC (XBridge C18 column
- washeluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min)
Sources & evidence
- ORD record
- ord-f09372b3fb3b435ca211466adcb8c66e
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388185B2
Reaction notes
Loading…