Chlorosuccinimide → HCID 69253473, compound

HRID 746803Notes

Reaction equation

HRID 746803 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][CH:20]=[CH:21][C:22]=2[NH:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[CH:14][CH:13]=1)#[N:2].[Cl:30]N1C(=O)CCC1=O>O1CCCC1>[Cl:30][C:20]1[S:19][C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:4]3[CH:5]=[CH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:3]=3[C:1]#[N:2])=[CH:17][CH:16]=2)=[C:22]([NH:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[CH:21]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 24769562HCID 24769562, compound

Product 1

HCID 69253473HCID 69253473, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-cyano-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-carboxylic acid (0.021 g) in dry tetrahydrofuran (0.5 mL) at 0° C. and add N-chlorosuccinimide (0.007 g). Allow the reaction mixture to reach RT and stir for 72 h. Add diethyl ether, concentrate in vacuo and purify by Strata® silica gel cartridges, eluting with dichloromethane-methanol gradient. Purify by reverse phase HPLC to give 0.004 g of the title compound as a white solid. MS (ES−) (m/z): 459 (M−1).

Workup

  1. customto reach RT
  2. concentrationAdd diethyl ether, concentrate in vacuo
  3. custompurify by Strata® silica gel cartridges
  4. washeluting with dichloromethane-methanol gradient
  5. customPurify by reverse phase HPLC

Sources & evidence

ORD record
ord-7c756fe279314db9b24dbee1cd4a469e
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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