Chlorosuccinimide → HCID 66897365, compound

HRID 2044130Notes

Reaction equation

HRID 2044130 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:14][S:15]([C:18]1[C:19]2[CH:20]=[CH:21][NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:17])=[O:16])[CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]#[N:13].CC(SCC[NH2+]C(CN)=O)=O.C([O-])(C(F)(F)F)=O.C1C(=O)N([Cl:53])C(=O)C1>CN(C=O)C.CC#N>[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:14][S:15]([C:18]1[C:19]2[C:20]([Cl:53])=[CH:21][NH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:17])=[O:16])[CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]#[N:13]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 57219S-acetyl-N-glycylcysteamineHCID 66897272HCID 66897272, compound

Product 1

HCID 66897365HCID 66897365, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 0.20 g (0.52 mmol) of 4-(2-cyano-pyrrol-1-yl)-2-(1H-indole-4-sulfonylamino)-butyric acid methyl ester (from the synthesis of I-102) and 0.070 g (0.52 mmol) of NCS in 1 mL of DMF is stirred overnight, and then diluted with MeCN and purified by preparative HPLC to provide 0.15 g (0.36 mmol; 69%) of 2-(3-chloro-1H-indole-4-sulfonylamino)-4-(2-cyano-pyrrol-1-yl)-butyric acid methyl ester. This material is stirred in 1.4 mL of THF with 1.4 mL of 1M NaOH for 3 h, and then 2N HCl is added until the pH is 3. The mixture is extracted with EtOAc, and the extract washed with brine, dried over Na2SO4, filtered, and concentrated to provide 0.12 g (85%) of I-103 as a tan powder.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-96dffca45bf84fa2b227af2e5e7b47e7
Source dataset
uspto-grants-2013_11
Patent number
US08586748B2

Reaction notes

Loading…