Ethanol → 2-((5,5-Diethoxy-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)piperidin-2-yl)methyl)isoindoline-1,3-dione

HRID 60831Notes

Reaction equation

HRID 60831 reaction equation
[CH2:1]([O:3][C:4]1([O:27][CH2:28][CH3:29])[CH2:9][N:8]([C:10]([C:12]2[N:13]=[C:14]([CH3:24])[S:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:11])[CH:7](CO)[CH2:6][CH2:5]1)[CH3:2].[CH3:30][CH2:31][OH:32]>>[CH2:1]([O:3][C:4]1([O:27][CH2:28][CH3:29])[CH2:9][N:8]([C:10]([C:12]2[N:13]=[C:14]([CH3:24])[S:15][C:16]=2[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[O:11])[CH:7]([CH2:7][N:8]2[C:31](=[O:32])[C:30]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:10]2=[O:11])[CH2:6][CH2:5]1)[CH3:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 89739753(5,5-Diethoxy-2-(hydroxymethyl)piperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

Product 1

HCID 897411382-((5,5-Diethoxy-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)piperidin-2-yl)methyl)isoindoline-1,3-dione

Procedure

The title compound was prepared according to general procedure I using rac-(5,5-diethoxy-2-(hydroxymethyl)piperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone. 1H NMR (CDCl3, 400 MHz) δ 7.73-7.71 (m, 2H), 7.63-7.62 (m, 2H), 7.38-7.35 (m, 2H), 7.21-6.91 (m, 2H), 4.86-4.81 (m, 1H), 4.10-4.03 (m, 2H), 3.10 (d, 1H), 2.27 (s, 3H), 1.89-1.83 (m, 1H), 1.70-1.61 (m, 1H), 1.32-1.28 (m, 2H), 1.19-1.03 (m, 6H). MS (ESI) 506 (M+H): desired product lost EtOH in LC/MS.

Sources & evidence

ORD record
ord-c07429e21a9747b9ad7de58186f468e6
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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