2-Phthalimidoethanesulfonyl chloride → HCID 66625058, compound

HRID 416516Notes

Reaction equation

HRID 416516 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[O:17]=[C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[N:19]1[CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31]>>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([CH2:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[S:30]([CH2:29][CH2:28][N:19]2[C:18](=[O:17])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:27])(=[O:31])=[O:32])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 61284214HCID 61284214, compound

Product 1

HCID 66625058HCID 66625058, compound

Procedure

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-amide was prepared by an analogous procedure as described for example 1 i) starting from 217 mg (0.91 mmol) (1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-amine and 250 mg (1 equiv.) 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride. Purification by flash chromatography on silica gel (eluent: CH2Cl2/MeOH) gave pure 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-amide as a light yellow foam. Yield: 178 mg MS (ES+): m/e=477.

Workup

  1. custom2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-amide was prepared by an analogous procedure
  2. customPurification by flash chromatography on silica gel (eluent: CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-fe0d92918bf14aa7a9f73f6b76ab4116
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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