Hydrochloric Acid → (3-Amino-2,5,6-trifluorophenyl)(3-morpholinoquinoxalin-6-yl)methanone

HRID 929349Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of N-(2,4,5-trifluoro-3-(3-morpholinoquinoxaline-6-carbonyl)phenyl)pivalamide (560 mg, 1.2 mmol, 1.0 eq.) in HOAc (10 mL) was added conc. HCl (50 mL). The mixture was stirred at 110° C. for 4 h, then poured onto ice. The mixture was adjusted to pH 10 by the addition of 1N NaOH solution, then extracted with DCM (100 mL×3). The combined organic layers were dried over Na2SO4 and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/4, v/v) to afford (3-amino-2,5,6-trifluorophenyl)(3-morpholinoquinoxalin-6-yl)methanone as brown solid (410 mg, 88% yield).

Workup

additionpoured onto ice
extractionextracted with DCM (100 mL×3)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe resulting residue was purified by flash column chromatography (PE/EA=1/4, v/v)

Sources & evidence

ORD record: ord-bbbe9c2779414808809e510daebd3eb3
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09295671B2

Reaction notes

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