Diisopropylethylamine → HCID 118037121, compound
Reaction equation
[NH2:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[O:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH2:18])[CH2:13][CH2:12]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:9]=[C:8]([NH:18][CH2:17][CH:14]2[CH2:15][CH2:16][O:11][CH2:12][CH2:13]2)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
6-amino-4-fluoronicotinonitrile (intermediate 21, 50 mg, 0.365 mmol) and (tetrahydro-2H-pyran-4-yl)methanamine (84 mg, 0.729 mmol) were dissolved in NMP (1 ml) and treated at room temperature with DIPEA (0.219 ml, 1.09 mmol). The reaction mixture was then stirred at 50° C. for 4 h and at 90° C. for 4 h. The reaction mixture was cooled to room temperature, quenched with water and diluted with EtOAc. The layers were separated and organic layer was washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as an off-white solid. (UPLC-MS 3) tR 0.40 min; ESI-MS 233.1 [M+H]+.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customquenched with water
- additiondiluted with EtOAc
- customThe layers were separated
- washorganic layer was washed with water and brine
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)
Sources & evidence
- ORD record
- ord-1ff481ee51f44201bdb194c2aa304f5c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266883B2
Reaction notes
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