Morpholine → HCID 58522467, compound

HRID 718046Notes

Reaction equation

Cl[C:2]1=[N:3][C:4]2[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=2[O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=3)=[CH:9][C:8]1=2.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:31]1[CH2:32][CH2:33][N:28]([C:2]2=[N:3][C:4]3[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=3[O:6][C:7]3[CH:12]=[CH:11][C:10]([C:13]4[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=4)=[CH:9][C:8]2=3)[CH2:29][CH2:30]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirring solution of title compound 69 (285 mg, 0.754 mmol) in toluene (5.0 mL) was added morpholine (1.00 g, 11.48 mmol) and the reaction mixture was stirred at 130° C. for 4 h. It was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography with 10%-30% ethyl acetate in hexanes to afford title compound 70 (223 mg, 69%) as a white solid. LRMS (ESI): (calc) 428.17. (found) 429.5 (MH)+. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.09 (d, J=8.6 Hz, 2H), 7.84 (dd, J=8.4, 2.3 Hz, 1H), 7.71-7.69 (m, 3H), 7.40 (d, J=8.4 Hz, 1H), 7.17-7.01 (m, 4H), 4.38 (q, J=7.1 Hz, 2H), 3.90-3.75 (m, 4H), 3.60-3.48 (m, 4H), 1.40 (t, J=7.1 Hz, 3H).

Workup

temperatureIt was cooled to room temperature
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude was purified by flash chromatography with 10%-30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-34e00db2b72c406cb9816f9cae5886ff
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193749B2

Reaction notes

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