Diisopropylethylamine → [2-Amino-6-(1-methanesulfonyl-piperidin4-ylamino)-pyridin-3-yl]-(2-methoxy-phenyl)-methanone
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.FC(F)(F)C(O)=O.[CH3:26][S:27]([N:30]1[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]1)(=[O:29])=[O:28].C(N(CC)C(C)C)(C)C>C(O)C>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:9])=[CH:6][CH:5]=[C:4]([NH:36][CH:33]2[CH2:34][CH2:35][N:30]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:31][CH2:32]2)[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of (2-Amino-6-chloro-pyridin-3-yl)-(2-methoxy-phenyl)-methanone (24.9 mg, 0.0948 mmol, Example 5), 1-methanesulfonyl-piperidin-4-ylamine (50.6 mg, 0.284 mmol, from Step A above), N,N-diisopropylethylamine (38mg, 0.294 mmol) and ethanol (2.7 mL) were heated at 160-180° C. in a sealed tube under microwave conditions for 0.5-4 hrs. The resulting reaction mixture was concentrated in vacuo and the residue was purified on silica gel with methylene chloride/methanol to give [2-Amino-6-(1-methanesulfonyl-piperidin4-ylamino)-pyridin-3-yl]-(2-methoxy-phenyl)-methanone as a white solid (22.5 mg, 58% yield). HRMS, observed: 405.1594, calcd for (M+H)+: 405.1591.
Workup
- customThe resulting reaction mixture
- concentrationwas concentrated in vacuo
- customthe residue was purified on silica gel with methylene chloride/methanol
Sources & evidence
- ORD record
- ord-3fb66c85643a4206bf9bf188018e6fe1
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423051B2
Reaction notes
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