2-Phthalimidoethanesulfonyl chloride → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (3,4,5,6-tetrahydro-2h[1,4']bipyridinyl-4-yl)-amide

HRID 416498Notes

Reaction equation

HRID 416498 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[O:14]=[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[N:16]1[CH2:25][CH2:26][S:27](Cl)(=[O:29])=[O:28]>>[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH:4]([NH:7][S:27]([CH2:26][CH2:25][N:16]2[C:15](=[O:14])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:24])(=[O:28])=[O:29])[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 189186081-(Pyridin-4-yl)piperidin-4-amine

Product 1

HCID 666244022-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (3,4,5,6-tetrahydro-2h[1,4']bipyridinyl-4-yl)-amide

Procedure

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (3,4,5,6-tetrahydro-2H[1,4′]bipyridinyl-4-yl)-amide was prepared by an analogous procedure as described for example 1 i) starting from 638 mg (3.6 mmol) 3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-ylamine and 985 mg (1 equiv.) 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride. The product was obtained in crude form as a light yellow foam. Yield: 860 mg MS (ES+): m/e=415.

Workup

  1. customThe product was obtained in crude form as a light yellow foam

Sources & evidence

ORD record
ord-99d3fc0231914859a551c0d7f33b7c21
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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