Phenylsulphonyl isocyanate → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-{[(phenylsulfonyl)amino]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)-1H-indole-7-carboxamide

HRID 1806515Notes

Reaction equation

HRID 1806515 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]4[C:16](=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=3)[NH:15][CH:14]=[C:13]4[CH:22]3[CH2:27][CH2:26][N:25]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[C:33]1([S:39]([N:42]=[C:43]=[O:44])(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CS(C)=O>[CH2:31]([S:28]([N:25]1[CH2:26][CH2:27][CH:22]([C:13]2[C:12]3[C:16](=[C:17]([C:19]([NH2:21])=[O:20])[CH:18]=[C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[CH2:1][N:2]([C:43]([NH:42][S:39]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)(=[O:41])=[O:40])=[O:44])[CH2:3]5)[CH:11]=3)[NH:15][CH:14]=2)[CH2:23][CH2:24]1)(=[O:29])=[O:30])[CH3:32]

Participants

4

Reactant 2

HCID 76096Phenylsulphonyl isocyanateHCID 42630496HCID 42630496, compound

Product 1

HCID 577327473-[1-(ethylsulfonyl)-4-piperidinyl]-5-(2-{[(phenylsulfonyl)amino]carbonyl}-2,3-dihydro-1H-isoindol-5-yl)-1H-indole-7-carboxamideYield 36.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-(2,3-dihydro-1H-isoindol-5-yl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (30 mg, 0.066 mmol) in DMSO (1.0 mL), was added benzenesulfonyl isocyanate (15 mg, 0.079 mmol). The resultant mixture was stirred overnight at room temperature. Mixture purified by Gilson Preparatory HPLC to give 15.5 mg of the title compound.

Workup

  1. customMixture purified by Gilson Preparatory HPLC

Sources & evidence

ORD record
ord-f16077c90462462a89871949a26336e2
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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