1,3-dioxo-2-(prop-2-en-1-yl)-2,3-dihydro-1H-isoindole-5-carboxylic acid → (S)-2-allyl-1,3-dioxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)isoindoline-5-carboxamide

HRID 2370787

Reaction equation

HRID 2370787 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([OH:16])=O)[CH:10]=2)[C:5]1=[O:17])[CH:2]=[CH2:3].Cl.[F:19][C:20]([F:40])([F:39])[C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]([C:29]2[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][N:30]=2)[NH2:28])=[CH:23][CH:22]=1>>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([NH:28][C@@H:27]([C:24]3[CH:25]=[CH:26][C:21]([C:20]([F:40])([F:19])[F:39])=[CH:22][CH:23]=3)[C:29]3[C:34]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:32]=[CH:31][N:30]=3)=[O:16])[CH:10]=2)[C:5]1=[O:17])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 35075911,3-dioxo-2-(prop-2-en-1-yl)-2,3-dihydro-1H-isoindole-5-carboxylic acid2×HCID 86687962(S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine Hydrochloride

Product 1

HCID 86687965(S)-2-allyl-1,3-dioxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)isoindoline-5-carboxamide

Procedure

2-Allyl-1,3-dioxoisoindoline-5-carboxylic acid was then coupled with Intermediate 1 using the general methods described above for the amide coupling reaction (Table 2) to provide the title compound, (S)-2-allyl-1,3-dioxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)isoindoline-5-carboxamide as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 8.93 (d, J=3.9 Hz, 1H), 8.44 (d, J=7.6 Hz, 1H), 8.30-8.21 (m, 2H), 8.11-8.02 (m, 1H), 7.98-7.89 (m, 1H), 7.64-7.46 (m, 5H), 6.88 (d, J=7.6 Hz, 1H), 5.99-5.75 (m, 1H), 5.34-5.15 (m, 2H), 4.31 (d, J=5.7 Hz, 2H). MS (ESI pos. ion) m/z: 534.1 (M+H).

Sources & evidence

ORD record
ord-c64cb55175504f838356e948d5a2e737
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Linked notes

Loading…