Methanesulfonyl chloride → HCID 20222398, compound

HRID 980302Notes

Reaction equation

HRID 980302 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][NH2:25])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][NH:25][S:27]([CH3:26])(=[O:29])=[O:28])[CH:22]=2)[NH:17][CH:16]=1)[CH3:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20222395HCID 20222395, compound

Product 1

HCID 20222398HCID 20222398, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-methylethyl]-1H-indole-5-methanamine (3.29 g) in dry pyridine (50 ml) cooled in an ice bath was treated with methanesulphonyl chloride (1.64 ml). After 18 h at room temperature the solvent was removed under reduced pressure and the resulting viscous orange oil poured into a mixture of ice and concentrated hydrochloric acid (200 ml) to give a pink solid which was purified by chromatography on kieselgel 60 (200 g) eluted with ethyl acetate/cyclohexanane (1:1) to give the title compound as a yellow foam (0.28 g). This material was used without further purification.

Workup

  1. customAfter 18 h at room temperature the solvent was removed under reduced pressure
  2. additionthe resulting viscous orange oil poured into a mixture of ice and concentrated hydrochloric acid (200 ml)
  3. customto give a pink solid which
  4. customwas purified by chromatography on kieselgel 60 (200 g)
  5. washeluted with ethyl acetate/cyclohexanane (1:1)

Sources & evidence

ORD record
ord-2ee17856facc4397977d679c3ee69e34
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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