Chlorosuccinimide → HCID 68289747, compound

HRID 878752Notes

Reaction equation

HRID 878752 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][N:11]([C:26]3[N:27]=[CH:28][C:29]4[C:34]([C:35]=3[CH3:36])=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:12]([C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=2)[CH:3]=[CH:2]1.[Cl:37]N1C(=O)CCC1=O>O1CCCC1>[Cl:37][C:3]1[C:4]2[C:9](=[CH:8][C:7]([CH2:10][N:11]([C:26]3[N:27]=[CH:28][C:29]4[C:34]([C:35]=3[CH3:36])=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)(=[O:14])=[O:13])=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68290200HCID 68290200, compound

Product 1

HCID 68289747HCID 68289747, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{[(1H-indol-6-ylmethyl)(4-methylisoquinolin-3-yl)amino]sulfonyl}benzoate (177 mg, 0.36 mmol) prepared in Example 116 in tetrahydrofuran (1.8 mL) was added N-chlorosuccinimide (57 mg, 0.43 mmol) at room temperature, and the mixture was stirred for 17 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1) to give ethyl 4-{[[(3-chloro-1H-indol-6-yl)methyl] (4-methylisoquinolin-3-yl)amino]sulfonyl}benzoate (124 mg, 65%) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1)

Sources & evidence

ORD record
ord-294953422a6041a485ac3751c9745f5d
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

Loading…