Diisopropylethylamine → HCID 70664890, compound

HRID 1403546Notes

Reaction equation

Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[O:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>CS(C)=O.ClCCl>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([NH:29][CH:26]3[CH2:27][CH2:28][O:23][CH2:24][CH2:25]3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200.0 mg, 0.63 mmol) in DMSO (1.5 mL) was added tetrahydro-2H-pyran-4-amine (127.8 mg, 1.26 mmol), DIEA (163.3 mg, 1.27 mmol) under nitrogen atmosphere. After stirring overnight at 100° C., the reaction mixture was dissolved in dichloromethane (30 mL), washed with water (3×10 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 0.01%-0.1% ethyl acetate in petroleum ether to afford methyl 2-(4-fluorophenyl)-3-(tetrahydro-2H-pyran-4-ylamino)quinoxaline-6-carboxylate as a light yellow solid (180.0 mg, 75%).

Workup

washwashed with water (3×10 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto afford a residue, which
customwas purified by a silica gel column with 0.01%-0.1% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-20f41b3f0dcd464b9b258dd30d9bfa73
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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