Morpholine → 5-(1-Hydroxy-2-morpholinoethyl)-4'-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide

HRID 1845342Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Into a 20 mL reaction vessel were combined 4′-methyl-N-((6-methylpyridin-3-yl)methyl)-5-(oxiran-2-yl)biphenyl-3-carboxamide (15 mg, 0.042 mmol), ethanol (2 mL), and morpholine (13 mg, 0.15 mmol). The mixture was heated at 50° C. overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH]) to afford the title product.

Workup

customInto a 20 mL reaction vessel
customThe volatiles were removed under reduced pressure
customthe residue was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH])

Sources & evidence

ORD record: ord-b552b99b9ccb4e4d97e181eb4202ddd9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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