(3S)-3-methylmorpholine → HCID 25254223, compound

HRID 219479Notes

Reaction equation

HRID 219479 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].[CH3:30][C@H:31]1[CH2:36][O:35][CH2:34][CH2:33][NH:32]1>>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:32]2[CH2:33][CH2:34][O:35][CH2:36][C@@H:31]2[CH3:30])=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

Participants

3

Reactant 2

HCID 12012220(3S)-3-methylmorpholineHCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 25254223HCID 25254223, compoundYield 65%

Procedure

Example 8a (74 mg, 0.16 mmol) was reacted with (S)-3-methylmorpholine (3.0 eq.) as described under General Procedure G and the crude mixture was purified by flash chromatography (silica gel, hexane/Et2O 1:4) to afford the title compound as a pale yellow oil (51 mg, 65%). 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.05 (t, J=6.0 Hz, 2H), 3.95 (t, J=6.6 Hz, 2H), 3.83 (s, 3H), 3.79-3.57 (m, 4H), 3.22 (dd, J=8.7, 11.1 Hz, 1H), 3.12-2.88 (m, 2H), 2.74 (m, 1H), 2.55-2.35 (m, 6H), 2.18 (s, 3H), 2.07-1.96 (m, 2H), 1.29 (d, J=6.9 Hz, 3H), 0.96 (d, J=6.0 Hz, 3H). MS (ES+) m/z 508.2 (M+H+).

Workup

  1. customthe crude mixture was purified by flash chromatography (silica gel, hexane/Et2O 1:4)

Sources & evidence

ORD record
ord-2df3f7f94e00459cb982acefe474967b
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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