Triethylamine → HCID 58547731, compound
Reaction equation
[Br:1][C:2]1[C:3]([O:9][CH:10]2[CH2:13][N:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.C(N(CC)CC)C>CS(C)=O>[Br:1][C:2]1[C:3]([O:9][CH:10]2[CH2:13][N:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[CH2:11]2)=[N:4][C:5]([N:24]2[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]2)=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a mixture of 2-(3-((5-bromo-2-chloropyrimidin-4-yl)oxy)azetidin-1-yl)quinoline (see PREPARATION P2.11; 0.1 g, 0.25 mmol) and piperidin-4-yl-methanol (0.028 g, 0.25 mmol) was added DMSO (2 mL) and triethylamine (0.05 g, 0.50 mmol). The solution was heated to 150° C. under microwave for 3 hours. The mixture was then extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in hexanes) to give the title product (0.02 g, 0.04 mmol, 17% yield) as white solid. ESI-MS (M+1): 471 calc. for C22H24BrN5O2 470.
Workup
- extractionThe mixture was then extracted with EtOAc (2×20 mL)
- washThe combined organic extracts were washed with water (10 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe filtrate was evaporated in vacuo
- customthe residue was purified by flash column chromatography on silica gel (20% to 60% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-02d3b4ed4f1d4e99a3c7a53d63c49ba0
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376450B2
Reaction notes
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