Morpholine → HCID 46916411, compound

HRID 2045929Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol) in EtOH (5 mL), morpholine (63 μL, 0.706 mmol) was added and the reaction mixture was heated at 100° C. for 20 hrs. Upon completion, the solvent was removed in vacuo and the crude oily residue was purified by preparative LCMS to afford 2-morpholino-N-(3-(quinoxalin-2-yl)phenyl)acetamide (35 mg, 30% yield). LCMS calculated for C20H20N4O2 (M+H): 349.40. found 349. 1H-NMR (DMSO-d6, 400 Mhz) δH: 9.98 (1H, br.), 9.53 (1H, s), 8.55 (1H, m), 8.13-8.20 (2H, m), 8.05-8.08 (1H, m), 7.82-7.98 (3H, m), 7.55-7.60 (1H, m), 3.70 (4H, m), 3.20 (2H, s), 2.58 (4H, m).

Workup

customUpon completion, the solvent was removed in vacuo
customthe crude oily residue was purified by preparative LCMS

Sources & evidence

ORD record: ord-a9c6bc131fe6494fa96f1a854853cbfb
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592415B2

Reaction notes

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